Name: 6311-22-4|9-Methyl-9H-fluoren-9-ol|98%
Brand: Ambeed
SKU: A703811
Rating: 92 (22 reviews)

1
[ 108-31-6 ]
[ 6311-22-4 ]
[ 13913-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride

Reference： [1]Campbell; Wang [Journal of the Chemical Society, 1949, p. 1513]

2
[ 917-64-6 ]
[ 486-25-9 ]
[ 6311-22-4 ]

Yield	Reaction Conditions	Operation in experiment
91%
91%		7 The synthesis of 4 starts from commercially available 9-fluorenone, which is methylated using MeMgl forming 26. This compound was then converted into 9-methyl-9W-fluorene by acid catalyzed dehydration in refluxing glacial acetic acid followed by overnight reduction using Pd/C and H2 (1 atm - balloon) in a one pot procedure. 9-Methyl-9W-fluorene was obtained in a 67% yield (2 steps) starting from 20 grams of 9-fluorenone ( 111 mmol). 9-Methyl-9AY-fiuorene was subsequently used to capture gaseous C02 after deprotonation using n-BuLi in cold THF. Using excess C02 resulted in a total isolated yield of 91% of the acid precursor 27 after recrystallization . 9-Methyl-9H- fluorene was also used for the capture of [13C]-C02 applied as limiting reagent, resulting in a 73% isolated yield of 27. 27 and 27 was then transformed quantitatively into their acid chloride derivatives 4 and *4 using oxalyl chloride and a ca DMF in CH2CI2 at 30 °C.
	With diethyl ether

	In diethyl ether at 0℃;
	Stage #1: methyl magnesium iodide; 9-fluorenone In tetrahydrofuran; diethyl ether at 0 - 20℃; Stage #2: With water; sodium hydroxide In tetrahydrofuran; diethyl ether at 0℃;
	In tetrahydrofuran; diethyl ether at 0 - 20℃;

Reference： [1]Location in patent: scheme or table Hermange, Philippe; Lindhardt, Anders T.; Taaning, Rolf H.; Bjerglund, Klaus; Lupp, Daniel; Skrydstrup, Troels [Journal of the American Chemical Society, 2011, vol. 133, # 15, p. 6061 - 6071]
[2]Current Patent Assignee: AARHUS UNIVERSITY - WO2012/79583, 2012, A1 Location in patent: Page/Page column 77
[3]Ullmann; v. Wurstemberger [Chemische Berichte, 1905, vol. 38, p. 4107] Daufresne [Bulletin de la Societe Chimique de France, 1907, vol. <4> 1, p. 1236] Ferrer [Anales de la Real Sociedad Espanola de Fisica y Quimica, vol. 20, p. 462][Chemisches Zentralblatt, 1923, vol. 94, # III, p. 1161]
[4]Hammons,J.H. [Journal of Organic Chemistry, 1968, vol. 33, # 3, p. 1123 - 1127] Browne,S.E.; Asher,S.E.; Cornwall,E.H. [Journal of the American Chemical Society, 1984, vol. 106, p. 1432] Meyers, Cal Y.; Lutfi, Hisham G.; Varol, Pninit; Hou, Yuqing; Robinson, Paul D. [Acta Crystallographica, Section C: Crystal Structure Communications, 2000, vol. 56, # 12, p. 1468 - 1470]
[5]Amyes, Tina L.; Richard, John P.; Novak, Michael [Journal of the American Chemical Society, 1992, vol. 114, # 21, p. 8032 - 8041]
[6]Location in patent: experimental part Vougioukalakis, Georgios C.; Roubelakis, Manolis M.; Orfanopoulos, Michael [Journal of Organic Chemistry, 2010, vol. 75, # 12, p. 4124 - 4130]
[7]Malliaros, Nikitas G.; Orfanopoulos, Michael [European Journal of Organic Chemistry, 2021, vol. 2021, # 34, p. 4846 - 4850]

3
[ 486-25-9 ]
[ 75-16-1 ]
[ 6311-22-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran at 0 - 20℃; for 16h; Glovebox;	5 9-methyl-9H-fluoren-9-ol (Si). In a glovebox, a 250mL round-bottom flask was charged with 9H-fluoren-9-one (10.300 g, 57.2 mmol, 1.0 eq) and THF (8OmL), and the resultingsolution was cooled to 0°C. MeMgBr (20.0 mL of a 3.0 M solution, 0.6 mmol, 1.05 eq) was then slowly added using a syringe to the stirring solution, which turned into a slurry at the end of the addition. The mixture was warmed to room temperature and allowed to stir for 16 hours. The reaction vessel was then removed from the glovebox, and the reaction mixture was poured into a saturated solution of NH4C1 (200nth) and washed with brine (iOOmL x 2). Theorganic portion was collected, dried over MgSO4, filtered and concentrated under a nitrogenstream. The crude product was recrystallized in pentane (200nth) yielding Si (10.077 g, 90%)as a white powder. Alternatively, L5a can be purified on a BiotageTM silica column with agradient of 5-20% ethyl acetate in hexane.
89.06%	In tetrahydrofuran; diethyl ether at 0 - 20℃; Glovebox;	In the glove-box at 0 C., G-1, fluorenone, (30.00 g, 166.5 mmol) in tetrahydrofuran (70 mE) is added to methylmagnesium bromide (66.5 mE, 199.5 mmol) in diethyl ether (500 mE). The reaction solution is stirred at tt. overnight. The reaction solution is cooled to 00 C. and 200 mE of water is added. The solution is brought to a pH of 9 with 2M NaOH. The organic fraction is washed with brine (3x200 mE), dried with magnesium sulfate, filtered and concentrated in vacuo yielding the yellow oil, G-2 (29.10 g, 148.28 mmol, 89.06% yield).
88%	In diethyl ether for 2h; Heating;

88%	Stage #1: 9-fluorenone; methylmagnesium bromide In diethyl ether at 0 - 20℃; Schlenk technique; Inert atmosphere; Stage #2: With water; ammonium chloride In diethyl ether Schlenk technique; Inert atmosphere;
49%	In diethyl ether at 0 - 20℃; Inert atmosphere;
49%	In diethyl ether at 0℃; for 0.166667h;
	In tetrahydrofuran; diethyl ether at 0℃; for 4.5h;	I To a stirring solution of compound A (5 g, 27.7 mmol) in dry THF (60 mL) at 0° C., under N2, was added MeMgBr (3M in diethyl ether, 9.24 mL). The cooling bath was removed and the mixture was stirred for an additional 1.5 h. More MeMgBr (0.8 ml) was added to the reaction mixture followed by additional stirring for another 3 h. The reaction was carefully quenched with ice-water and extracted into ethyl acetate (3×100 mL). The combined organic layers were washed with brine (1×50 mL), dried (MgSO4), and concentrated to yield compound B (4.76 g): 1H-NMR (DMSO-d6) δ 7.73 (d, 2H), 7.53 (dd, 2H), 7.36-7.28 (m, 4H), 5.51 (s, 1H), 1.57 (s, 3H).
5.67 g	In tetrahydrofuran at 0℃; for 48h;	Synthesis of 9-methy-9H-fluoren-9-ol (1) In a glovebox, in a 50mL round bottom flask, 9H-fluorene-9-one (5.458g, 30.3mmol) was dissolved in 20 mL of THF and cooled to 0°C for 30 minutes. MeMgBr (1.2 eq.) was then slowly added via syringe while stirring. A slurry formed once all of the Grignard was added. The reaction was allowed to stir for 48 hours. The flask was then removed from the glovebox and 4mL of 2M NaOH were added. The mixture was washed with brine and the organic portion collected and dried over MgS04, filtered and the volatiles removed under a N2 stream. NMR of the resultant yellow solid showed pure 9-methyl-9H-fluoren-9-ol. Yield is 5.67g (95wt%).

Reference： [1]Current Patent Assignee: DOW INC - WO2016/153682, 2016, A1 Location in patent: Page/Page column 38
[2]Current Patent Assignee: EXXON MOBIL CORP - US2017/96508, 2017, A1 Location in patent: Paragraph 0203-0205
[3]Bowen, Martina E.; Reddy Aavula, Bhasker; Mash, Eugene A. [Journal of Organic Chemistry, 2002, vol. 67, # 25, p. 9087 - 9088]
[4]Liu, Xiaobing; Sheng, Heyun; Zhou, Yao; Song, Qiuling [Organic Letters, 2021, vol. 23, # 7, p. 2543 - 2547]
[5]Konstandaras, Nicholas; Dunn, Michelle H.; Guerry, Max S.; Barnett, Christopher D.; Cole, Marcus L.; Harper, Jason B. [Organic and Biomolecular Chemistry, 2019, vol. 18, # 1, p. 66 - 75]
[6]Cole, Marcus L.; Dunn, Michelle H.; Harper, Jason B.; Konstandaras, Nicholas; Luis, Ena T. [Organic and biomolecular chemistry, 2020, vol. 18, # 10, p. 1910 - 1917]
[7]Friedrich,E.C.; Taggart,D.B. [Journal of Organic Chemistry, 1978, vol. 43, # 5, p. 805 - 808] Wieland; Krause [Justus Liebigs Annalen der Chemie, 1925, vol. 443, p. 136]
[8]Vougioukalakis, Georgios C.; Orfanopoulos, Michael [Tetrahedron Letters, 2003, vol. 44, # 48, p. 8649 - 8652]
[9]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - US2005/234040, 2005, A1 Location in patent: Page/Page column 17
[10]Current Patent Assignee: EXXON MOBIL CORP - WO2015/88819, 2015, A1 Location in patent: Page/Page column 71

4
[ 1689-64-1 ]
[ 6311-22-4 ]
[ 3912-47-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; acetic acid

Reference： [1]Wawzonek; Dufek [Journal of the American Chemical Society, 1956, vol. 78, p. 3530,3532]

5
[ 2523-37-7 ]
[ 6311-22-4 ]

Yield	Reaction Conditions	Operation in experiment
54%	With lithium aluminium tetrahydride; oxygen In tetrahydrofuran at 0℃; for 2.5h; Reflux;
	With pyridine; benzene-trimethyl-ammonium hydroxide; oxygen
	With sodium hydroxide; potassium permanganate

Stage #1: 9-methylfluorene With triethylsilane; oxygen In acetonitrile for 1h; Irradiation; Stage #2: With triphenylphosphine

Reference： [1]Matviiuk, Tetiana; Menendez, Christophe; Carayon, Chantal; Saffon, Nathalie; Voitenko, Zoia; Lherbet, Christian; Baltas, Michel [European Journal of Organic Chemistry, 2014, vol. 2014, # 29, p. 6538 - 6546]
[2]Sprinzak [Journal of the American Chemical Society, 1958, vol. 80, p. 5449,5452]
[3]Wawzonek et al. [Journal of Organic Chemistry, 1956, vol. 21, p. 276]
[4]Lykakis, Ioannis N.; Orfanopoulos, Michael [Tetrahedron Letters, 2005, vol. 46, # 45, p. 7835 - 7839]

6
[ 6311-22-4 ]
[ 3955-65-5 ]
[ 103161-83-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen azide; chloroform; sulfuric acid
	With sodium azide; chloroform; sulfuric acid

Reference： [1]Arcus; Coombs [Journal of the Chemical Society, 1954, p. 4319,4327] Coombs [Journal of the Chemical Society, 1958, p. 3454,3456]
[2]Arcus; Coombs [Journal of the Chemical Society, 1954, p. 4319,4327] Coombs [Journal of the Chemical Society, 1958, p. 3454,3456]

7
[ 6311-22-4 ]
[ 2523-37-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃;
90%	With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃;
76%	Stage #1: 9-methyl-9H-fluoren-9-ol In acetic acid Heating; Stage #2: With hydrogen In acetic acid at 20℃; Further stages.;

74%	Stage #1: 9-methyl-9H-fluoren-9-ol With acetic acid Reflux; Stage #2: With hydrogen	7 The synthesis of 4 starts from commercially available 9-fluorenone, which is methylated using MeMgl forming 26. This compound was then converted into 9-methyl-9W-fluorene by acid catalyzed dehydration in refluxing glacial acetic acid followed by overnight reduction using Pd/C and H2 (1 atm - balloon) in a one pot procedure. 9-Methyl-9W-fluorene was obtained in a 67% yield (2 steps) starting from 20 grams of 9-fluorenone ( 111 mmol). 9-Methyl-9AY-fiuorene was subsequently used to capture gaseous C02 after deprotonation using n-BuLi in cold THF. Using excess C02 resulted in a total isolated yield of 91% of the acid precursor 27 after recrystallization . 9-Methyl-9H- fluorene was also used for the capture of [13C]-C02 applied as limiting reagent, resulting in a 73% isolated yield of 27. 27 and 27 was then transformed quantitatively into their acid chloride derivatives 4 and *4 using oxalyl chloride and a ca DMF in CH2CI2 at 30 °C.
70%	With hydrogen In acetic acid for 1h; Heating;
45%	With H
	With hydrogen iodide; acetic acid
	With acetic acid anschliessende Hydrierung an Platin;
88 % Spectr.	With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran for 24h; ultrasonic irradiation;
	With zinc In acetic acid
	With iodine; hypophosphorous acid In acetic acid
	With triethylsilane; diethyl ether; boron trifluoride
	Multi-step reaction with 2 steps 1: aluminium phosphate / 250 °C / im Vakuum 2: palladium black; diethyl ether / Hydrogenation
	With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0℃; for 1h;
	Multi-step reaction with 2 steps 1: acetic acid / Reflux 2: palladium on carbon; hydrogen / 760.05 Torr
	With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0℃; for 1h;

Reference： [1]Konstandaras, Nicholas; Dunn, Michelle H.; Guerry, Max S.; Barnett, Christopher D.; Cole, Marcus L.; Harper, Jason B. [Organic and Biomolecular Chemistry, 2019, vol. 18, # 1, p. 66 - 75]
[2]Cole, Marcus L.; Dunn, Michelle H.; Harper, Jason B.; Konstandaras, Nicholas; Luis, Ena T. [Organic and biomolecular chemistry, 2020, vol. 18, # 10, p. 1910 - 1917]
[3]Bowen, Martina E.; Reddy Aavula, Bhasker; Mash, Eugene A. [Journal of Organic Chemistry, 2002, vol. 67, # 25, p. 9087 - 9088]
[4]Current Patent Assignee: AARHUS UNIVERSITY - WO2012/79583, 2012, A1 Location in patent: Page/Page column 77
[5]Rakus, Klaus; Verevkin, Sergej P.; Schaetzer, Juergen; Beckhaus, Hans-Dieter; Ruechardt, Christoph [Chemische Berichte, 1994, vol. 127, # 6, p. 1095 - 1104]
[6]Ziemnicka, B.; Doane, J. W. [Molecular Crystals and Liquid Crystals (1969-1991), 1987, vol. 150, p. 361 - 374]
[7]Wanscheidt; Moldavski [Chemische Berichte, 1931, vol. 64, p. 917,925][Zhurnal Obshchei Khimii, 1931, vol. 1, p. 304,324][Chemisches Zentralblatt, 1931, vol. 102, # II, p. 3208]
[8]Badger [Journal of the Chemical Society, 1941, p. 535,537]
[9]Karaman; Kohlman; Fry [Tetrahedron Letters, 1990, vol. 31, # 43, p. 6155 - 6158]
[10]Browne,S.E.; Asher,S.E.; Cornwall,E.H. [Journal of the American Chemical Society, 1984, vol. 106, p. 1432]
[11]Meyers, Cal Y.; Lutfi, Hisham G.; Varol, Pninit; Hou, Yuqing; Robinson, Paul D. [Acta Crystallographica, Section C: Crystal Structure Communications, 2000, vol. 56, # 12, p. 1468 - 1470]
[12]Vougioukalakis, Georgios C.; Orfanopoulos, Michael [Tetrahedron Letters, 2003, vol. 44, # 48, p. 8649 - 8652]
[13]Wieland; Reindel; Ferrer [Chemische Berichte, 1922, vol. 55, p. 3315]
[14]Location in patent: experimental part Vougioukalakis, Georgios C.; Roubelakis, Manolis M.; Orfanopoulos, Michael [Journal of Organic Chemistry, 2010, vol. 75, # 12, p. 4124 - 4130]
[15]Hermange, Philippe; Lindhardt, Anders T.; Taaning, Rolf H.; Bjerglund, Klaus; Lupp, Daniel; Skrydstrup, Troels [Journal of the American Chemical Society, 2011, vol. 133, # 15, p. 6061 - 6071]
[16]Malliaros, Nikitas G.; Orfanopoulos, Michael [European Journal of Organic Chemistry, 2021, vol. 2021, # 34, p. 4846 - 4850]

8
[ 6311-22-4 ]
[ 39194-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride nachf. Einw_. von Methanol;
	Multi-step reaction with 2 steps 1: diethyl ether; hydrogen chloride 2: 20 °C

Reference： [1]Nakamura [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1927, p. 118][Chemisches Zentralblatt, 1928, vol. 99, # I, p. 345]
[2]Wieland; Krause [Justus Liebigs Annalen der Chemie, 1925, vol. 443, p. 136]

9
[ 6311-22-4 ]
[ 123333-50-6 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; acetic anhydride

Reference： [1]Lavie; Bergmann [Journal of Organic Chemistry, 1953, vol. 18, p. 367,373]

10
[ 6311-22-4 ]
[ 15300-82-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; iodine; tin(ll) chloride weiteres Reagens: Essigsaeure;

Reference： [1]Wanscheidt; Moldavski [Chemische Berichte, 1931, vol. 64, p. 917,925][Zhurnal Obshchei Khimii, 1931, vol. 1, p. 304,324][Chemisches Zentralblatt, 1931, vol. 102, # II, p. 3208]

11
[ 6311-22-4 ]
[ 70402-38-9 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether; hydrogen bromide; magnesium sulfate at 0℃;

Reference： [1]Bartlett; Cohen [Journal of the American Chemical Society, 1940, vol. 62, p. 1183,1185]

12
[ 6311-22-4 ]
[ 188541-54-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; diethyl ether

Reference： [1]Wieland; Krause [Justus Liebigs Annalen der Chemie, 1925, vol. 443, p. 136]

13
[ 6311-22-4 ]
[ 100726-25-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With indium(III) bromide; trimethylsilylazide In dichloromethane at -10 - 25℃; Schlenk technique; Inert atmosphere;
	With sodium azide; chloroform; trichloroacetic acid

Reference： [1]Wei, Kaijie; Yang, Tonghao; Chen, Qing; Liang, Siyu; Yu, Wei [Chemical Communications, 2020, vol. 56, # 78, p. 11685 - 11688]
[2]Coombs [Journal of the Chemical Society, 1958, p. 3454,3456]

14
[ 6311-22-4 ]
(9-azido-fluoren-9-yl)-(9-methyl-fluoren-9-yl)-methane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide; chloroform; trichloroacetic acid

Reference： [1]Coombs [Journal of the Chemical Society, 1958, p. 3454,3456]

15
[ 6311-22-4 ]
[ 108-24-7 ]
acetic acid-(9-methyl-fluoren-9-yl ester) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Wieland; Cerezo [Justus Liebigs Annalen der Chemie, 1927, vol. 457, p. 255]

16
[ 19126-15-9 ]
[ 591-51-5 ]
[ 6311-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether Erhitzen der Reaktionsloesung auf 100grad und anschliessendes Behandeln mit Wasser;

Reference： [1]Wittig; Happe [Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 205,208, 216]

17
[ 6311-22-4 ]
[ 106-51-4 ]
[ 5779-80-6 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride

Reference： [1]Campbell; Wang [Journal of the Chemical Society, 1949, p. 1513]

18
[ 6311-22-4 ]
[ 130-15-4 ]
[ 72853-56-6 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride

Reference： [1]Campbell; Wang [Journal of the Chemical Society, 1949, p. 1513]

19
[ 50-00-0 ]
[ 6311-22-4 ]
[ 26060-12-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In acetic acid

Reference： [1]Kuhn,R. et al. [Justus Liebigs Annalen der Chemie, 1962, vol. 654, p. 64 - 81]

20
[ 91-01-0 ]
[ 6311-22-4 ]
[ 5751-46-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In acetic acid

Reference： [1]Kuhn,R. et al. [Justus Liebigs Annalen der Chemie, 1962, vol. 654, p. 64 - 81]

21
[ 486-25-9 ]
[ 15681-48-8 ]
[ 6311-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether

Reference： [1]House,H.O.; Umen,M.J. [Journal of the American Chemical Society, 1972, vol. 94, p. 5495 - 5497]

22
[ 6311-22-4 ]
[ 94879-55-7 ]
[ 5542-59-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In acetic acid Heating;

Reference： [1]Kuhn,R. et al. [Justus Liebigs Annalen der Chemie, 1965, vol. 689, p. 1 - 20]
[2]Kuhn,R.; Fischer,H. [Angewandte Chemie, 1964, vol. 76, p. 146]

23
[ 6311-22-4 ]
1,1,5,5-Bis-biphenylen-penten-⁽²⁾-diol-(1,5) [ No CAS ]
[ 4612-67-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In acetic acid

Reference： [1]Kuhn,R. et al. [Justus Liebigs Annalen der Chemie, 1965, vol. 689, p. 1 - 20]

24
[ 6311-22-4 ]
[ 103623-02-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In acetic acid

Reference： [1]Kuhn,R. et al. [Justus Liebigs Annalen der Chemie, 1962, vol. 654, p. 64 - 81]

25
[ 67-56-1 ]
[ 6311-22-4 ]
[ 2523-37-7 ]
[ 39194-34-8 ]
[ 4425-82-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 6% 2: 10% 3: 55%	In water Irradiation;
1: 55% 2: 6% 3: 10%	In water Irradiation;

Reference： [1]Wan, Peter; Krogh, Erik [Journal of the American Chemical Society, 1989, vol. 111, # 13, p. 4887 - 4895]
[2]Wan, Peter; Krogh, Erik [Journal of the American Chemical Society, 1989, vol. 111, # 13, p. 4887 - 4895]

26
[ 67-56-1 ]
[ 6311-22-4 ]
[ 39194-34-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	for 24h; Ambient temperature;
	With toluene-4-sulfonic acid Ambient temperature;

Reference： [1]Strazzolini, Paolo; Giumanini, Angelo G.; Verardo, Giancarlo [Tetrahedron, 1994, vol. 50, # 1, p. 217 - 254]
[2]Amyes, Tina L.; Richard, John P.; Novak, Michael [Journal of the American Chemical Society, 1992, vol. 114, # 21, p. 8032 - 8041]

27
[ 106-44-5 ]
[ 6311-22-4 ]
4-methyl-2-(9-methyl-9H-fluoren-9-yl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With sulfuric acid In dichloromethane at 20℃; for 3h;	5 4-methyl-2-(9-methyl-9H-fluoren-9-yl)phenol (Si). In a SOOnth round-bottom flask, pcresol (7.8g, 72mmol, 2eq) was dissolved in DCM (200mL) followed by slow addition ofconcentrated sulfuric acid (3.916g, 37.93mmol, ieq). A solution of Si (7.403g, 37.72mmol,ieq) in DCM (i5OmL) was then added to the flask using an addition funnel, and the resultingyellow solution was stirred for 3 hours at room temperature during which the color turnedgreen. The reaction was basified with 2M NaOH to pH 9-10. The organic layer was collected,washed with brine, dried with Mg504 and concentrated under a nitrogen stream. The crude product was purified over a BiotageTM silica column using a gradient of 5-20% DCM in hexane, which yielded S2 (8.437g, 78%) as a white crystalline powder.
	With phosphoric acid or AlCl₃;
	With sulfuric acid In dichloromethane for 2h;	Synthesis of 4-methyl-2-(9-methyl-9H-fluoren-9-yl) phenol (2) In a 200mL round bottom flask, p-cresol (2.075g, 19.2mmol) and 2 (3.766g, 19.2mmol) were dissolved in 80mL of CH2C12. 4 mL of cone. H2S04 (5 eq.) were added dropwise to the solution while stirring to produce a dark purple solution. After two hours, the purple solution was added slowly to 100 mL of H20 forming a white/blue precipitate. 2M NaOH was then added dropwise until the pH reached 9-10. The slurry was then washed with CH2CI2 (3 x 100 mL). The organic portion was then collected and dried with MgS04. Volatiles were removed under N2 leaving a brownish residue. The resultant product was purified on a silica column using a 5- 10% gradient of EtOAc/Hexane.

With sulfuric acid In dichloromethane for 2h;

Synthesis of 4-methyl-2-(9-methyl-9H-fluoren-9-yl)phenol (2) 10190] In a 200 mE round bottom flask, p-cresol (2.075 g,19.2 mmol) and 2 (3.766 g, 19.2 mmol) are dissolved in 80 mE of CH2C12. 4 mE of conc. H2504 (5 eq.) are added dropwise to the solution while stirring to produce a dark purple solution. After two hours, the purple solution is added slowly to 100 mE of H20 forming a white/blue precipitate. 2M NaOH is then added dropwise until the pH reached 9-10. The slurry is then washed with CH2C12 (3x100 mE). The organic portion is then collected and dried with MgSO4. Volatiles are removed under N2 leaving a brownish residue. The resultant product is purified on a silica colunm using a 5-10% gradient of EtOAc/Hexane.

Reference： [1]Current Patent Assignee: DOW INC - WO2016/153682, 2016, A1 Location in patent: Page/Page column 38; 39
[2]Zhang, Wei; Jacobsen, Eric N. [Journal of Organic Chemistry, 1991, vol. 56, # 7, p. 2296 - 2298]
[3]Current Patent Assignee: EXXON MOBIL CORP - WO2015/88819, 2015, A1 Location in patent: Page/Page column 71; 72
[4]Current Patent Assignee: EXXON MOBIL CORP - US2017/96508, 2017, A1 Location in patent: Paragraph 0190

28
[ 75-89-8 ]
[ 6311-22-4 ]
9-methyl-9-(2,2,2-trifluoroethoxy)fluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride

Reference： [1]Lew, Calvin S. Q.; McClelland, Robert A.; Johnston, Linda J.; Schepp, Norman P. [Journal of the Chemical Society. Perkin transactions II, 1994, # 3, p. 395 - 398]

29
[ 6311-22-4 ]
[ 4425-82-5 ]

Yield	Reaction Conditions	Operation in experiment
15%	With acetonitrile Irradiation;
15%	With acetonitrile Irradiation;
	Multi-step reaction with 2 steps 1: diethyl ether; hydrogen chloride 2: 80 °C

	Multi-step reaction with 2 steps 1: diethyl ether; hydrogen chloride 2: 80 °C
	With acetic acid Reflux;
	Multi-step reaction with 4 steps 1.1: acetic acid / Reflux 1.2: 760.05 Torr 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere 2.2: 20 °C 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 3 h / 30 °C / Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine / bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri-tert-butyl phosphine / 1,4-dioxane / 4 h / 80 °C

Reference： [1]Wan, Peter; Krogh, Erik [Journal of the American Chemical Society, 1989, vol. 111, # 13, p. 4887 - 4895]
[2]Wan, Peter; Krogh, Erik [Journal of the American Chemical Society, 1989, vol. 111, # 13, p. 4887 - 4895]
[3]Wieland; Krause [Justus Liebigs Annalen der Chemie, 1925, vol. 443, p. 136]
[4]Wieland; Krause [Justus Liebigs Annalen der Chemie, 1925, vol. 443, p. 136]
[5]Location in patent: scheme or table Hermange, Philippe; Lindhardt, Anders T.; Taaning, Rolf H.; Bjerglund, Klaus; Lupp, Daniel; Skrydstrup, Troels [Journal of the American Chemical Society, 2011, vol. 133, # 15, p. 6061 - 6071]
[6]Current Patent Assignee: AARHUS UNIVERSITY - WO2012/79583, 2012, A1

30
[ 6311-22-4 ]
[ 4425-82-5 ]
[ 188541-54-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 90% 2: 10%	With acetyl chloride In dichloromethane 1.) 0 deg C, 2.) room temperature, 1 h;

Reference： [1]Strazzolini, Paolo; Giumanini, Angelo G.; Verardo, Giancarlo [Tetrahedron, 1994, vol. 50, # 1, p. 217 - 254]

31
[ 6311-22-4 ]
[ 4425-82-5 ]
[ 64666-57-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; 3,5-dinitrobenoyl chloride In dichloromethane for 4h; Ambient temperature; Title compound not separated from byproducts;

Reference： [1]Amyes, Tina L.; Richard, John P.; Novak, Michael [Journal of the American Chemical Society, 1992, vol. 114, # 21, p. 8032 - 8041]

32
[ 6311-22-4 ]
[ 20685-25-0 ]

Yield	Reaction Conditions	Operation in experiment
	With perchloric acid; sodium perchlorate In water at 25℃; also in 1percent aq. sol. of mercaptoethanol;
	With fluorosulfonylchloride; antimony pentafluoride In fluorosulphonic acid
	With fluorosulfonylchloride; antimony pentafluoride; fluorosulphonic acid at -78℃;

Reference： [1]Amyes, Tina L.; Richard, John P.; Novak, Michael [Journal of the American Chemical Society, 1992, vol. 114, # 21, p. 8032 - 8041]
[2]Arnett, Edward M.; Hofelich, Thomas C. [Journal of the American Chemical Society, 1983, vol. 105, # 9, p. 2889 - 2895]
[3]Olah,G.A.; Prakash,G.K.; Liang,G. [Journal of the American Chemical Society, 1980, vol. 102, p. 4485]

33
[ 6311-22-4 ]
[ 140483-62-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With caesium fluoroxysulphate In acetonitrile
	With caesium fluoroxysulphate In acetonitrile

Reference： [1]Stavber, Stojan; Kosir, Iztok; Zupan, Marko [Journal of the Chemical Society. Chemical communications, 1992, # 3, p. 274 - 275]
[2]Stavber, Stojan; Kosir, Iztok; Zupan, Marko [Journal of Fluorine Chemistry, 1991, vol. 54, # 1-3, p. 268]

34
[ 6311-22-4 ]
9-fluoromethyl-9-hydroxyfluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85 % Chromat.	With Selectfluor In acetonitrile for 0.5h;

Reference： [1]Stavber, Stojan; Zupan, Marko [Journal of the Chemical Society. Chemical communications, 1994, # 2, p. 149 - 150]

35
[ 19126-15-9 ]
[ 486-25-9 ]
[ 6311-22-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 81 % Chromat. 2: 17 % Chromat.	With potassium hydroxide In benzene at 80℃; for 34h; oth. phase-transfer catalyst, oth. solvent, oth. time, oth. base;

Reference： [1]Solov'yanov, A. A.; El-Said, Ahmed Ali Ahmed; Beletskaya, I. P.; Reutov, O. A. [Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 7, p. 1232 - 1243][Zhurnal Organicheskoi Khimii, 1987, vol. 23, # 7, p. 1365 - 1377]

36
[ 20685-25-0 ]
[ 6311-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	With perchloric acid; sodium perchlorate; water In various solvent(s) at 25℃; also in 1percent aq. sol. of mercaptoethanol;
	With water In various solvent(s) at 20℃;

Reference： [1]Amyes, Tina L.; Richard, John P.; Novak, Michael [Journal of the American Chemical Society, 1992, vol. 114, # 21, p. 8032 - 8041]
[2]Lew; Wagner; Angelini, Mark P.; Lee-Ruff; Lusztyk; Johnston [Journal of the American Chemical Society, 1996, vol. 118, # 48, p. 12066 - 12073]

37
[ 6311-22-4 ]
[ 99-33-2 ]
[ 4425-82-5 ]
[ 64666-57-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine In dichloromethane for 4h; Ambient temperature;

Reference： [1]Amyes, Tina L.; Richard, John P.; Novak, Michael [Journal of the American Chemical Society, 1992, vol. 114, # 21, p. 8032 - 8041]

38
[ 917-64-6 ]
[ 486-25-9 ]
[ 39194-34-8 ]
[ 6311-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran Yield given. Yields of byproduct given;
	In tetrahydrofuran Yield given;

Reference： [1]Lund, Torben; Pedersen, Morten L.; Frandsen, Lars A. [Tetrahedron Letters, 1994, vol. 35, # 49, p. 9225 - 9226]
[2]Lund, Torben; Pedersen, Morten L.; Frandsen, Lars A. [Tetrahedron Letters, 1994, vol. 35, # 49, p. 9225 - 9226]

39
[ 486-25-9 ]
[ 74-88-4 ]
[ 39194-34-8 ]
[ 6311-22-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	In N,N-dimethyl-formamide Yields of byproduct given;
	In N,N-dimethyl-formamide Yield given. Yields of byproduct given;

Reference： [1]Lund, Torben; Pedersen, Morten L.; Frandsen, Lars A. [Tetrahedron Letters, 1994, vol. 35, # 49, p. 9225 - 9226]
[2]Lund, Torben; Pedersen, Morten L.; Frandsen, Lars A. [Tetrahedron Letters, 1994, vol. 35, # 49, p. 9225 - 9226]

40
[ 486-25-9 ]
[3-(dimethylamino)propyl]dimethyl aluminium(III) [ No CAS ]
[ 4425-82-5 ]
[ 6311-22-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 88% 2: 4.7%	In toluene at 80℃; for 3h;

Reference： [1]Baidossi, Wael; Rosenfeld, Ayelet; Wassermann, Brigit C.; Schutte, Stefan; Schumann, Herbert; Blum, Jochanan [Synthesis, 1996, # 9, p. 1127 - 1130]

41
[ 6311-22-4 ]
Na<AlH2(OCH2CH2OMe)2> [ No CAS ]
[ 4569-45-3 ]

Reference： [1]Journal of Organometallic Chemistry,1975,vol. 84,p. 139 - 150

42
[ 6311-22-4 ]
[ 4425-82-5 ]

Yield	Reaction Conditions	Operation in experiment
	With monoaluminum phosphate at 250℃; im Vakuum;

Reference： [1]Wieland; Reindel; Ferrer [Chemische Berichte, 1922, vol. 55, p. 3315] Ferrer [Anales de la Real Sociedad Espanola de Fisica y Quimica, vol. 20, p. 463][Chemisches Zentralblatt, 1923, vol. 94, # III, p. 1161]

43
[ 6311-22-4 ]
[ 407-25-0 ]
9-methyl-9-fluorenyl trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-dimethylpyridine In diethyl ether at -10 - 0℃;

Reference： [1]Creary, Xavier; Burtch, Elizabeth A.; Jiang, Ziqi [Journal of Organic Chemistry, 2003, vol. 68, # 3, p. 1117 - 1127]

44
[ 2523-37-7 ]
[ 486-25-9 ]
[ 6311-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 9-methylfluorene With triethylsilane; [Bu₄N]4W₁₀O₃₂; oxygen In acetonitrile at 5 - 10℃; for 1h; Irradiation; Stage #2: With triphenylphosphine Further stages.;

Reference： [1]Lykakis, Ioannis N.; Orfanopoulos, Michael [Tetrahedron Letters, 2004, vol. 45, # 41, p. 7645 - 7649]

45
[ 6311-22-4 ]
[ 2365-48-2 ]
[ 866921-52-0 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid In dichloromethane at 20℃; for 18h;	I A mixture of compound B (1.5 g, 7.6 mmol), methyl thioglycolate (0.68 mL, 7.6 mmol) and trifluoroacetic acid (0.58 mL, 7.6 mmol) in CH2Cl2 (15 mL) was stirred at room temperature for 18 h, quenched with sat. sodium bicarbonate and extracted into CH2Cl2 (3×50 mL). The combined organic layers were washed with brine (1×50 mL), dried (MgSO4) and concentrated to give a crude product that was purified by silica gel column chromatography (hexane:ethyl acetate::8:1) to yield 1.8 g of product as a pale yellow solid: 1H-NMR (DMSO-d6) δ 7.84-7.82 (m, 2H), 7.57-7.55 (m, 2H), 7.41-7.34 (m, 4H), 3.21 (s, 3H), 2.58 (s, 2H), 1.71 (s, 3H).

Reference： [1]Current Patent Assignee: TEVA PHARMACEUTICAL INDUSTRIES LTD. - US2005/234040, 2005, A1 Location in patent: Page/Page column 17

46
[ 6311-22-4 ]
[ 954-71-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 45 percent / H 2: 81 percent / AlCl₃

Reference： [1]Ziemnicka, B.; Doane, J. W. [Molecular Crystals and Liquid Crystals (1969-1991), 1987, vol. 150, p. 361 - 374]

47
[ 6311-22-4 ]
[ 133295-76-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: H₃PO₄ / or AlCl₃ 2: SnCl₄, lutidine

Reference： [1]Zhang, Wei; Jacobsen, Eric N. [Journal of Organic Chemistry, 1991, vol. 56, # 7, p. 2296 - 2298]

48
[ 6311-22-4 ]
C₅₈H₄₈N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: H₃PO₄ / or AlCl₃ 2: SnCl₄, lutidine 3: ethanol / 1 h / Heating

Reference： [1]Zhang, Wei; Jacobsen, Eric N. [Journal of Organic Chemistry, 1991, vol. 56, # 7, p. 2296 - 2298]

49
[ 6311-22-4 ]
[ 3912-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: concentrated aqueous HCl; acetic acid 2: aqueous HI

Reference： [1]Wawzonek; Dufek [Journal of the American Chemical Society, 1956, vol. 78, p. 3530,3532]

50
[ 6311-22-4 ]
[ 74373-03-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: diethyl ether; hydrogen chloride 2: 80 °C 3: diethyl ether; petroleum ether; nitrogen dioxide 4: concentrated aqueous ammonia; alcohol 5: carbon disulfide; bromine / Sonnenlicht
	Multi-step reaction with 5 steps 1: diethyl ether; hydrogen chloride 2: 80 °C 3: diethyl ether; petroleum ether; nitrogen dioxide 4: concentrated aqueous ammonia; alcohol 5: carbon disulfide; bromine / Sonnenlicht

Reference： [1]Wieland; Krause [Justus Liebigs Annalen der Chemie, 1925, vol. 443, p. 136]
[2]Wieland; Krause [Justus Liebigs Annalen der Chemie, 1925, vol. 443, p. 136]

51
[ 6311-22-4 ]
[ 74373-02-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: diethyl ether; hydrogen chloride 2: 80 °C 3: diethyl ether; petroleum ether; nitrogen dioxide 4: concentrated aqueous ammonia; alcohol
	Multi-step reaction with 4 steps 1: diethyl ether; hydrogen chloride 2: 80 °C 3: diethyl ether; petroleum ether; nitrogen dioxide 4: concentrated aqueous ammonia; alcohol

Reference： [1]Wieland; Krause [Justus Liebigs Annalen der Chemie, 1925, vol. 443, p. 136]
[2]Wieland; Krause [Justus Liebigs Annalen der Chemie, 1925, vol. 443, p. 136]

52
[ 6311-22-4 ]
[ 858800-60-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine
	Multi-step reaction with 2 steps 1: MgSO₄; diethyl ether; HBr / 0 °C 2: 20 °C

Reference： [1]Wieland; Cerezo [Justus Liebigs Annalen der Chemie, 1927, vol. 457, p. 255]
[2]Bartlett; Cohen [Journal of the American Chemical Society, 1940, vol. 62, p. 1183,1185]

53
[ 6311-22-4 ]
[ 861373-30-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: diethyl ether; hydrogen chloride 2: 80 °C 3: diethyl ether; petroleum ether; nitrogen dioxide
	Multi-step reaction with 3 steps 1: diethyl ether; hydrogen chloride 2: 80 °C 3: diethyl ether; petroleum ether; nitrogen dioxide

Reference： [1]Wieland; Krause [Justus Liebigs Annalen der Chemie, 1925, vol. 443, p. 136]
[2]Wieland; Krause [Justus Liebigs Annalen der Chemie, 1925, vol. 443, p. 136]

54
[ 6311-22-4 ]
[ 60930-50-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. HCl / acetic acid 2: H₂ / Pd-C / acetic acid

Reference： [1]Kuhn,R. et al. [Justus Liebigs Annalen der Chemie, 1962, vol. 654, p. 64 - 81]

55
[ 6311-22-4 ]
[ 875214-66-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. HCl / acetic acid 2: aq. KOH

Reference： [1]Kuhn,R. et al. [Justus Liebigs Annalen der Chemie, 1962, vol. 654, p. 64 - 81]

56
[ 6311-22-4 ]
[ 96376-97-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. HCl / acetic acid 2: aq. KOH

Reference： [1]Kuhn,R. et al. [Justus Liebigs Annalen der Chemie, 1962, vol. 654, p. 64 - 81]

57
[ 6311-22-4 ]
[ 96271-13-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. HCl / acetic acid 2: Cl₂

Reference： [1]Kuhn,R. et al. [Justus Liebigs Annalen der Chemie, 1962, vol. 654, p. 64 - 81]

58
[ 6311-22-4 ]
[(13C)]-9-methyl-9H-fluorene-9-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: acetic acid / Reflux 2.1: palladium on carbon; hydrogen / 760.05 Torr 3.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere 3.2: -78 - 20 °C
	Multi-step reaction with 2 steps 1.1: acetic acid / Reflux 1.2: 760.05 Torr 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere 2.2: 20 °C

Reference： [1]Hermange, Philippe; Lindhardt, Anders T.; Taaning, Rolf H.; Bjerglund, Klaus; Lupp, Daniel; Skrydstrup, Troels [Journal of the American Chemical Society, 2011, vol. 133, # 15, p. 6061 - 6071]
[2]Current Patent Assignee: AARHUS UNIVERSITY - WO2012/79583, 2012, A1

59
[ 6311-22-4 ]
[ 1072315-89-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: acetic acid / Reflux 2.1: palladium on carbon; hydrogen / 760.05 Torr 3.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere 3.2: -78 - 20 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 30 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: acetic acid / Reflux 1.2: 760.05 Torr 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere 2.2: 20 °C 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 3 h / 30 °C / Inert atmosphere

Reference： [1]Hermange, Philippe; Lindhardt, Anders T.; Taaning, Rolf H.; Bjerglund, Klaus; Lupp, Daniel; Skrydstrup, Troels [Journal of the American Chemical Society, 2011, vol. 133, # 15, p. 6061 - 6071]
[2]Current Patent Assignee: AARHUS UNIVERSITY - WO2012/79583, 2012, A1

60
[ 6311-22-4 ]
C₁₆H₁₅NOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: hydrogen bromide / water / 0.5 h / 60 °C / Reflux 2: sodium hydroxide / 1 h / 80 °C 3: 2 h / Reflux 4: thionyl chloride / benzene / 3 h / Reflux 5: ammonium hydroxide / dichloromethane / 0.5 h / 0 - 20 °C

Reference： [1]Dunn, Derek; Hostetler, Greg; Iqbal, Mohamed; Marcy, Val R.; Lin, Yin Guo; Jones, Bruce; Aimone, Lisa D.; Gruner, John; Ator, Mark A.; Bacon, Edward R.; Chatterjee, Sankar [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 11, p. 3751 - 3753]

61
[ 6311-22-4 ]
C₁₄H₁₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hydrogen bromide / water / 0.5 h / 60 °C / Reflux 2: sodium hydroxide / 1 h / 80 °C

Reference： [1]Dunn, Derek; Hostetler, Greg; Iqbal, Mohamed; Marcy, Val R.; Lin, Yin Guo; Jones, Bruce; Aimone, Lisa D.; Gruner, John; Ator, Mark A.; Bacon, Edward R.; Chatterjee, Sankar [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 11, p. 3751 - 3753]

62
[ 6311-22-4 ]
C₁₆H₁₃ClOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: hydrogen bromide / water / 0.5 h / 60 °C / Reflux 2: sodium hydroxide / 1 h / 80 °C 3: 2 h / Reflux 4: thionyl chloride / benzene / 3 h / Reflux

Reference： [1]Dunn, Derek; Hostetler, Greg; Iqbal, Mohamed; Marcy, Val R.; Lin, Yin Guo; Jones, Bruce; Aimone, Lisa D.; Gruner, John; Ator, Mark A.; Bacon, Edward R.; Chatterjee, Sankar [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 11, p. 3751 - 3753]

63
[ 6311-22-4 ]
C₁₆H₁₄O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: hydrogen bromide / water / 0.5 h / 60 °C / Reflux 2: sodium hydroxide / 1 h / 80 °C 3: 2 h / Reflux

Reference： [1]Dunn, Derek; Hostetler, Greg; Iqbal, Mohamed; Marcy, Val R.; Lin, Yin Guo; Jones, Bruce; Aimone, Lisa D.; Gruner, John; Ator, Mark A.; Bacon, Edward R.; Chatterjee, Sankar [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 11, p. 3751 - 3753]

64
[ 6311-22-4 ]
C₁₆H₁₅NO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: hydrogen bromide / water / 0.5 h / 60 °C / Reflux 2: sodium hydroxide / 1 h / 80 °C 3: 2 h / Reflux 4: thionyl chloride / benzene / 3 h / Reflux 5: ammonium hydroxide / dichloromethane / 0.5 h / 0 - 20 °C 6: dihydrogen peroxide / acetic acid / 2 h / 20 °C

Reference： [1]Dunn, Derek; Hostetler, Greg; Iqbal, Mohamed; Marcy, Val R.; Lin, Yin Guo; Jones, Bruce; Aimone, Lisa D.; Gruner, John; Ator, Mark A.; Bacon, Edward R.; Chatterjee, Sankar [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 11, p. 3751 - 3753]

65
[ 6311-22-4 ]
[ 17356-08-0 ]
[ 1379795-34-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide In water at 60℃; for 0.5h; Reflux;

Reference： [1]Location in patent: scheme or table Dunn, Derek; Hostetler, Greg; Iqbal, Mohamed; Marcy, Val R.; Lin, Yin Guo; Jones, Bruce; Aimone, Lisa D.; Gruner, John; Ator, Mark A.; Bacon, Edward R.; Chatterjee, Sankar [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 11, p. 3751 - 3753]

66
[ 6311-22-4 ]
[ 3300-17-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: acetic acid / Reflux 1.2: 760.05 Torr 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere 2.2: 20 °C

Reference： [1]Current Patent Assignee: AARHUS UNIVERSITY - WO2012/79583, 2012, A1

67
[ 6311-22-4 ]
[ 82102-37-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: acetic acid / Reflux 1.2: 760.05 Torr 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere 2.2: 20 °C 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 3 h / 30 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: AARHUS UNIVERSITY - WO2012/79583, 2012, A1

68
[ 6311-22-4 ]
[ 1285695-27-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: acetic acid / Reflux 1.2: 760.05 Torr 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere 2.2: 20 °C 3.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 3 h / 30 °C / Inert atmosphere 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate / tetrahydrofuran / Inert atmosphere; sealed tube 4.2: 48 h / 25 °C / Inert atmosphere; sealed tube

Reference： [1]Current Patent Assignee: AARHUS UNIVERSITY - WO2012/79583, 2012, A1

69
[ 1450-14-2 ]
[ 6311-22-4 ]
[ 2523-37-7 ]
[ 1403992-17-5 ]

Yield	Reaction Conditions	Operation in experiment
	With 1% Au/TiO2 In ethyl acetate at 55℃; for 1h; Overall yield = 96 %;

Reference： [1]Gryparis, Charis; Stratakis, Manolis [Chemical Communications, 2012, vol. 48, # 87, p. 10751 - 10753,3]

70
[ 6311-22-4 ]
[ 104-94-9 ]
[ 1574305-96-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tantalum pentafluoride In toluene at 110℃; for 2.5h;	General Procedure for benzylation of amines with benzyl alcohols General procedure: Aryl amines 1 (1 eq), benzyl alcohols 2 (1 eq) and dry toluene, TaF5 (0.1eq) was added. The mixture was stirred at 110 °C for 2.5 h and after completion of the reaction (TLC), the solvent was distilled under reduced pressure and the residue was passed through column chromatography (60-120 mesh silica gel, ethyl acetate : hexane = 1:20), the corresponding N-alkyl amines was obtained in good yields. The product was characterized by the following spectral data.

Reference： [1]Gangaram, Sathaiah; Adimulam, Chandra Shekhar; Akula, Ravi Kumar; Kengiri, Raju; Pamulaparthy, Shanthan Rao; Madabhushi, Sridhar; Banda, Narsaiah [Chemistry Letters, 2013, vol. 42, # 12, p. 1522 - 1524]

71
C₈₈H₁₀₄Ca₄O₁₃ [ No CAS ]
[ 74-88-4 ]
[ 6311-22-4 ]

Yield	Reaction Conditions	Operation in experiment
74%	In tetrahydrofuran at -78 - 20℃; for 1h; Schlenk technique; Inert atmosphere;

Reference： [1]Wei, Baosheng; Li, Heng; Zhang, Wen-Xiong; Xi, Zhenfeng [Organometallics, 2015, vol. 34, # 7, p. 1339 - 1344]

72
[ 6311-22-4 ]
[6,6'-(ethane-1,2-diylbis(methylazanediyl)) bis(methylene)bis(4-methyl-2-(9-methyl-9H-fluoren-9-yl)phenolate)]zirconium(IV)dibenzyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sulfuric acid / dichloromethane / 2 h 2: ethanol / 16 h / Reflux 3: toluene / 1 h
	Multi-step reaction with 3 steps 1: sulfuric acid / dichloromethane / 2 h 2: formaldehyd / ethanol / 16 h / Reflux 3: toluene / 1 h

Reference： [1]Current Patent Assignee: EXXON MOBIL CORP - WO2015/88819, 2015, A1
[2]Current Patent Assignee: EXXON MOBIL CORP - US2017/96508, 2017, A1

73
[ 6311-22-4 ]
6,6'-(ethane-1,2-diylbis(methylazanediyl)) bis(methylene)bis(4-methyl-2-(9-methyl-9H-fluoren-9-yl)phenol) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sulfuric acid / dichloromethane / 2 h 2: ethanol / 16 h / Reflux
	Multi-step reaction with 2 steps 1: sulfuric acid / dichloromethane / 2 h 2: formaldehyd / ethanol / 16 h / Reflux

Reference： [1]Current Patent Assignee: EXXON MOBIL CORP - WO2015/88819, 2015, A1
[2]Current Patent Assignee: EXXON MOBIL CORP - US2017/96508, 2017, A1

74
[ 2523-37-7 ]
[ 6311-22-4 ]
[ 15300-82-0 ]

Yield	Reaction Conditions	Operation in experiment
1: 56% 2: 47%	With lithium aluminium tetrahydride In tetrahydrofuran at 4℃; for 3h; Reflux;

Reference： [1]Matviiuk, Tetiana; Menendez, Christophe; Carayon, Chantal; Saffon, Nathalie; Voitenko, Zoia; Lherbet, Christian; Baltas, Michel [European Journal of Organic Chemistry, 2014, vol. 2014, # 29, p. 6538 - 6546]

75
[ 3240-34-4 ]
[ 6311-22-4 ]
(9-hydroxy-9H-fluoren-9-yl)methyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With acetic acid at 100℃; for 12h; regioselective reaction;

Reference： [1]Zhao, Chun-Yang; Li, Liang-Gui; Liu, Qing-Rong; Pan, Cheng-Xue; Su, Gui-Fa; Mo, Dong-Liang [Organic and Biomolecular Chemistry, 2016, vol. 14, # 28, p. 6795 - 6803]

76
[ 6311-22-4 ]
2-dimethylamino-N,N-bis[methylene(4-methyl-2-(9-methyl-9H-fluoren-9-yl)phenolate)]ethanamine zirconium(IV) dibenzyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sulfuric acid / dichloromethane / 3 h / 20 °C 2: lithium chloride / ethanol / 72 h / 80 °C 3: toluene / 3 h / 60 °C / Glovebox