[ CAS No. 66073-54-9 ] {[proInfo.proName]}

Name: 66073-54-9|2-Chloro-6-fluorobenzamide|98%
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Product Details of [ 66073-54-9 ]

CAS No. :	66073-54-9	MDL No. :	MFCD00055436
Formula :	C₇H₅ClFNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KLOZZZNFJYMTNE-UHFFFAOYSA-N
M.W :	173.57	Pubchem ID :	98564
Synonyms :

Safety of [ 66073-54-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 66073-54-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 66073-54-9 ]

[ 66073-54-9 ] Synthesis Path-Downstream 1~40

1
[ 79-37-8 ]
[ 66073-54-9 ]
[ 71791-39-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	In dichloromethane at 45 - 50℃; for 24h;
78%	In 1,2-dichloro-ethane at 40 - 50℃; for 22h;
2 g	In 1,2-dichloro-ethane for 24h; Reflux;	8.2 Preparation of 2-chloro-6-fluorobenzoyl isocyanate To a solution of 2-chloro-6-fluorobenzamide (2.0 g, 0.011 mmol) in EDC (10 mL) was added oxalyl chloride (2.18 g, 0.017 mmol). The reaction mass was refluxed for 24 h. Excess of solvent was removed under vacuum to afford 2.0 g of desired product.

Reference： [1]Balicki, Roman; Sobotka, Wieslaw; Ejmocki, Zdzislaw [Polish Journal of Chemistry, 1991, vol. 65, # 5-6, p. 1049 - 1053]
[2]Balicki, R.; Kaczmarek, L.; Sobotka, W.; Ejmocki, Z. [Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 6, p. 995 - 998]
[3]Current Patent Assignee: ICHNOS SCIENCES INC - WO2013/186692, 2013, A1 Location in patent: Page/Page column 65

2
[ 668-45-1 ]
[ 66073-54-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sulfuric acid at 75℃; for 3.5h;
80%	With sulfuric acid at 70℃; for 4h;
	With dihydrogen peroxide; potassium carbonate In dimethyl sulfoxide at 0 - 25℃;

5.5 g

With sulfuric acid at 60 - 70℃;

8.1 Preparation 2-chloro-6-fluorobenzamide A solution of 2-chloro-6-fluorobenzonitrile (8.0 g, 51.61 mmol) in cone, sulphuric acid (50 mL) was heated at 60-70°C for 6-7 h. The reaction mass was quenched in water and extracted with DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 5.5 g of desired product.

Reference： [1]Balicki, R.; Kaczmarek, L.; Sobotka, W.; Ejmocki, Z. [Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 6, p. 995 - 998]
[2]Balicki, Roman; Sobotka, Wieslaw; Ejmocki, Zdzislaw [Polish Journal of Chemistry, 1991, vol. 65, # 5-6, p. 1049 - 1053]
[3]Ni, Shuaishuai; Yuan, Yaxia; Huang, Jin; Mao, Xiaona; Lv, Maosheng; Zhu, Jin; Shen, Xu; Pei, Jianfeng; Lai, Luhua; Jiang, Hualiang; Li, Jian [Journal of Medicinal Chemistry, 2009, vol. 52, # 17, p. 5295 - 5298]
[4]Current Patent Assignee: ICHNOS SCIENCES INC - WO2013/186692, 2013, A1 Location in patent: Page/Page column 64; 65

3
[ 66073-54-9 ]
[ 3320-83-0 ]
[ 125230-38-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In N,N-dimethyl-formamide 1.) 30 min., -10 to 0 deg C, 2.) 4h, room temperature;

Reference： [1]Richter, Monika; Richter, Wolfgang; Pallas, Manfred [Zeitschrift fur Chemie, 1989, vol. 29, # 6, p. 204 - 205]

4
[ 66073-54-9 ]
[ 2493-02-9 ]
[ 116800-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In N,N-dimethyl-formamide 1.) 30 min., -10 to 0 deg C, 2.) 4h, room temperature;

Reference： [1]Richter, Monika; Richter, Wolfgang; Pallas, Manfred [Zeitschrift fur Chemie, 1989, vol. 29, # 6, p. 204 - 205]

5
[ 75-15-0 ]
[ 66073-54-9 ]
[ 74-88-4 ]
[ 119448-98-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1) -20 degC; Yield given. Multistep reaction;

Reference： [1]Richter, Monika; Richter, Wolfgang [Zeitschrift fur Chemie, 1988, vol. 28, # 8, p. 292 - 293]

6
[ 75-15-0 ]
[ 66073-54-9 ]
[ 74-88-4 ]
[ 119448-95-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1) -20 degC; Yield given. Multistep reaction;

Reference： [1]Richter, Monika; Richter, Wolfgang [Zeitschrift fur Chemie, 1988, vol. 28, # 8, p. 292 - 293]

Yield	Reaction Conditions	Operation in experiment
	2-Chlor-6-fluor-benzonitril, wss. H2SO4;
		1.58 N-(2-methoxvbenzvl)-2-chloro-6-fluorobenzamide Example 1(58) N-(2-methoxvbenzvl)-2-chloro-6-fluorobenzamide TLC:Rf 0.40 (ethyl acetate: n-hexane = 3: 7); NMR (CDCl3):δ 7.38 (dd, J = 7.5, 1.5 Hz, 1H), 7.32-7.26 (m, 2H), 7.21-7.17 (m, 1H), 7.05-6.93 (m, 2H), 6.89 (d, J = 8.1 Hz, 1H), 6.27 (brs, 1H), 4.67 (d, J = 5.7 Hz, 2H), 3.85 (s, 3H).

8
[ 910473-61-9 ]
[ 66073-54-9 ]
C₁₃H₉ClFN₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With sodium hydride In tetrahydrofuran at 20℃; for 1h;	2.e Compound 13 was prepared according to the procedure outlined in Scheme 2. The ester was reduced with sodium borohydride (step (a)) and the product alcohol was converted to the corresponding aldehyde utilizing Dess- Martin reagent (step (b)). The aldehyde was condensed with 2-chloro-6- fluorobenzylamine in the presence of anhydrous magnesium sulfate to give an imine, which was subsequently reduced with sodium triacetoxyborohydride to give the secondary amine 13 (step (c)). The imide derivative 16 was also prepared starting with a carboxylic acid which was first converted to the corresponding acid chloride (step (d)). This material was then allowed to react with the anion of 2-chloro-6-fluorobenzamide generated with sodium hydride to give imide 16 in 34% yield (step (e)).
	With sodium hydride In tetrahydrofuran at 20℃; for 1h;

Reference： [1]Current Patent Assignee: MASS GENERAL BRIGHAM INC; HARVARD UNIVERSITY; BOSTON UNIVERSITY; TRUSTEES OF TUFTS COLLEGE, INC. - WO2009/23272, 2009, A1 Location in patent: Page/Page column 34
[2]Teng, Xin; Keys, Heather; Jeevanandam, Arumugasamy; Porco Jr., John A.; Degterev, Alexei; Yuan, Junying; Cuny, Gregory D. [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 24, p. 6836 - 6840]

9
[ 66073-54-9 ]
[ 116800-84-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1) NaH / 1) -20 degC 2: 68 percent / Na

Reference： [1]Richter, Monika; Richter, Wolfgang [Zeitschrift fur Chemie, 1988, vol. 28, # 8, p. 292 - 293]

10
[ 66073-54-9 ]
[ 139391-99-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 92 percent / CH₂Cl₂ / 24 h / 45 - 50 °C 2: 96 percent / benzene / 4 h / 40 °C

Reference： [1]Balicki, Roman; Sobotka, Wieslaw; Ejmocki, Zdzislaw [Polish Journal of Chemistry, 1991, vol. 65, # 5-6, p. 1049 - 1053]

11
[ 66073-54-9 ]
[ 139392-02-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 92 percent / CH₂Cl₂ / 24 h / 45 - 50 °C 2: 69 percent / CH₂Cl₂ / 6 h / Ambient temperature

Reference： [1]Balicki, Roman; Sobotka, Wieslaw; Ejmocki, Zdzislaw [Polish Journal of Chemistry, 1991, vol. 65, # 5-6, p. 1049 - 1053]

12
[ 66073-54-9 ]
[ 139392-03-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 92 percent / CH₂Cl₂ / 24 h / 45 - 50 °C 2: 55 percent / CH₂Cl₂ / 6 h / Ambient temperature

Reference： [1]Balicki, Roman; Sobotka, Wieslaw; Ejmocki, Zdzislaw [Polish Journal of Chemistry, 1991, vol. 65, # 5-6, p. 1049 - 1053]

13
[ 18871-66-4 ]
[ 66073-54-9 ]
[ 475155-76-1 ]

Yield	Reaction Conditions	Operation in experiment
	for 1h; Heating / reflux;	2 Reference Example 2; 3-(2-chloro-6-fluorophenyl)-5-methyl-1H-1,2,4-triazole Reference Example 2 3-(2-chloro-6-fluorophenyl)-5-methyl-1H-1,2,4-triazole The mixture of 2-chloro-6-fluorobenzamide (4.00 g, 23.0 mmol) and N,N-dimethylacetamide dimethylacetal (13 ml) was stirred under reflux with heating for 1 hour.. The residue obtained by concentration under reduced pressure was washed with petroleum ether to give yellow crystals (5.66 g).. The resulting crystals were suspended in toluene (40 ml), and hydrazine hydrate (2.23 ml, 46 mmol) was added thereto, then the solution was refluxed with heating for 4 hours.. To the reaction mixture was added ice-water (40 ml), and the precipitated crystals were collected by filtration.. The obtained crystals were recrystallized from ethyl acetate to give 3-(2-chloro-6-fluorophenyl)-5-methyl-1H-1,2,4-triazole (1.80 g, 8.51 mmol, 37%) as colorless crystals. mp: 232-233°C1H NMR (DMSO-d6) δ ppm: 2.43 (3H, s), 7.31-7.45 (3H, m), 13.90 (1H, br)19F NMR (DMSO-d6) δ ppm: -110.1 - -110. 2 (m) IR (nujol) ν cm-1: 3300, 3189, 3079, 1664,1633,1604, 1576, 1519, 1455, 1252, 902, 792 3-(2,6-dichlorophenyl)-5-methyl-1H-1,2,4-triazole (mp:221-226°C) and 3-(2,6-difluorophenyl)-5-methyl-1H-1,2,4-triazole (mp: 195-198°C) were synthesised according to the same manner.

Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - EP1386915, 2004, A1 Location in patent: Page 36-37

14
[ 110-91-8 ]
[ 939-97-9 ]
[ 66073-54-9 ]
4-(4-tert-butylphenyl)-2-(2-chloro-6-fluorophenyl)-5,6-dihydro-4H-1,3-oxazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In ice-water; dichloromethane	2 Example 2 STR18 (without intermediate isolation of the compound (II)) 3.5 g (20 mmol) of 2-chloro-6-fluorobenzamide are stirred with 3.4 g (21 mmol) of 4-tert-butylbenzaldehyde and 2.1 g (24 mmol) of morpholine for 18 hours at 50° C. in 40 ml of dichloromethane. After cooling, the reaction mixture is treated with 45 ml of titanium(IV) chloride (1-molar solution in dichloromethane) and, in an autoclave, saturated with dry hydrogen chloride gas at room temperature. Thereupon, ethylene is passed in at approximately 0° C. for approximately 20 to 30 minutes, and the mixture is subsequently stirred for 24 hours at 70° C. at an inherent pressure of approximately 14 bar. The reaction mixture is stirred with approximately 150 ml of ice-water, rendered alkaline at 0° C. using sodium hydroxide solution and extracted repeatedly using dichloromethane. The combined organic phases are dried over magnesium sulphate and concentrated. 1.38 g (30% of theory) of 4-(4-tert-butylphenyl)-2-(2-chloro-6-fluorophenyl)-5,6-dihydro-4H-1,3-oxazine of a logP of 4.71 are obtained.

Reference： [1]Current Patent Assignee: BAYER AG - US5892030, 1999, A

15
[ 110-91-8 ]
[ 939-97-9 ]
[ 66073-54-9 ]
N-[morpholin-4-yl-(4-tert-butylphenyl)-methyl]-2-chloro-6-fluoro-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; ice-water	II.a.2 Example (IIa-2) STR261 3.5 g (20 mmol) of 2-chloro-6-fluorobenzamide are stirred for 18 hours at 50° C. with 3.4 g (21 mmol) of 4-tert-butyl-benzaldehyde and 2.1 g (24.1 mmol) of morpholine in 30 ml of methanol. After cooling, the reaction mixture is stirred with 100 ml of ice-water, and the precipitate is filtered off with suction, washed with water and dried. 6.3 g (77.4% of theory) of N-[morpholin-4-yl-(4-tert-butylphenyl)-methyl]-2-chloro-6-fluoro-benzamide of melting point 180°-181° C. are obtained.

Reference： [1]Current Patent Assignee: BAYER AG - US5892030, 1999, A

16
3-fluoro-4-trifluoromethyl-phenyl isocyanate [ No CAS ]
[ 66073-54-9 ]
1-(2-chloro-6-fluorobenzoyl)-3-(3-fluoro-4-trifluoromethyl-phenyl)-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene	2 EXAMPLE 2 STR10 (Process variant (b)) EXAMPLE 2 STR10 (Process variant (b)) A solution of 2.05 g (0.01 mol) of 3-fluoro-4-trifluoromethyl-phenyl isocyanate in 10 ml of dry toluene are added to a solution of 1.74 g (0.01 mol) of 2-chloro-6-fluoro-benzamide in 40 ml of dry toluene at 60° C. with exclusion of moisture, and the mixture is refluxed for 7 hours. The solvent is subsequently removed in vacuo, and the residue is stirred with cold ether and separated off. The product is dried in vacuo. 3.1 g (82% of theory) of 1-(2-chloro-6-fluorobenzoyl)-3-(3-fluoro-4-trifluoromethyl-phenyl)-urea of melting point 200° C. are obtained.

Reference： [1]Current Patent Assignee: BAYER AG - US4782090, 1988, A

17
5-trifluoromethyl-2-pyridinylaminocarboxylic acid, phenyl ester [ No CAS ]
[ 66073-54-9 ]
1-(2-chloro-6-fluorobenzoyl)-3-(5-trifluoromethyl-2-pyridinyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		19 1-(2-CHLORO-6-FLUOROBENZOYL)-3-(5-TRIFLUOROMETHYL-2-PYRIDINYL)UREA EXAMPLE 19 1-(2-CHLORO-6-FLUOROBENZOYL)-3-(5-TRIFLUOROMETHYL-2-PYRIDINYL)UREA A portion of 2-chloro-6-fluorobenzamide is reacted with 5-trifluoromethyl-2-pyridinylaminocarboxylic acid, phenyl ester, in an inert organic solvent at elevated temperature to produce the product named in the heading above, identical to the product of Example 4, which is isolated by evaporating the reaction mixture and recrystallizing the product.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US4281003, 1981, A

18
[ 95651-16-4 ]
[ 66073-54-9 ]
1-(2-chloro-6-fluorobenzoyl)-3-(5-trifluoromethyl-2-pyridinyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		11 1-(2-CHLORO-6-FLUOROBENZOYL)-3-(5-TRIFLUOROMETHYL-2-PYRIDINYL)UREA EXAMPLE 11 1-(2-CHLORO-6-FLUOROBENZOYL)-3-(5-TRIFLUOROMETHYL-2-PYRIDINYL)UREA A portion of 2-chloro-6-fluorobenzamide is reacted with 5-trifluoromethyl-2-pyridinyl isocyanate as described in Example 8, and the product is isolated as described in that example to obtain the compound named above, identical to the product of Example 4.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US4281003, 1981, A

19
[ 66073-54-9 ]
5-chloro-2-isocyanatopyridine [ No CAS ]
1-(2-chloro-6-fluorobenzoyl)-3-(5-chloro-2-pyridinyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		10 1-(2-CHLORO-6-FLUOROBENZOYL)-3-(5-CHLORO-2-PYRIDINYL)UREA EXAMPLE 10 1-(2-CHLORO-6-FLUOROBENZOYL)-3-(5-CHLORO-2-PYRIDINYL)UREA A portion of 2-chloro-6-fluorobenzamide is reacted with 5-chloro-2-pyridinyl isocyanate as described in Example 8, and the product is isolated and purified as described in that example to obtain a significant yield of the product named in the heading, identical to the product of Example 3.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US4281003, 1981, A

20
[ 156778-47-1 ]
[ 97-97-2 ]
[ 66073-54-9 ]
N-(1-methoxy-2-chloroethyl)-2-fluoro-6-chlorobenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		9 Synthesis of N-(1-methoxy-2-chloroethyl)-2-fluoro-6-chlorobenzamide Example 9 Synthesis of N-(1-methoxy-2-chloroethyl)-2-fluoro-6-chlorobenzamide Utilizing a manufacturing method identical to that of preferred embodiment 2, 7.3 g of compound (8) was obtained from 6.5 g of 2-fluoro-6-chlorobenzamide and 23.0 g of chloroacetaldehyde dimethyl acetal. melting point: 134.8 - 135.5°C 1H - NMR (60 MHz, CDCl3, TMS) δ: 3.50 (s, 3H), 3.65 (d, 2H, J = 5.8 Hz), 5.20 - 5.58 (m, 1H), 6.85 - 7.50 (m, 3H), 8.55 - 9.00 (br, 1H)

Reference： [1]Current Patent Assignee: KYOYU AGRI CO.,LTD. - EP594179, 1994, A1

21
[ 66073-54-9 ]
[ 131056-82-1 ]
[ 1186372-20-2 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene at 110℃; for 10h;

Reference： [1]Ni, Shuaishuai; Yuan, Yaxia; Huang, Jin; Mao, Xiaona; Lv, Maosheng; Zhu, Jin; Shen, Xu; Pei, Jianfeng; Lai, Luhua; Jiang, Hualiang; Li, Jian [Journal of Medicinal Chemistry, 2009, vol. 52, # 17, p. 5295 - 5298]

22
[ 66073-54-9 ]
[ 107-11-9 ]
[ 1221408-06-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In N,N-dimethyl acetamide at 140℃;

Reference： [1]Location in patent: scheme or table Ahmad, Saleem; Ngu, Khehyong; Miller, Keith J.; Wu, Ginger; Hung, Chen-pin; Malmstrom, Sarah; Zhang, Ge; O'Tanyi, Eva; Keim, William J.; Cullen, Mary Jane; Rohrbach, Kenneth W.; Thomas, Michael; Ung, Thao; Qu, Qinling; Gan, Jinping; Narayanan, Rangaraj; Pelleymounter, Mary Ann; Robl, Jeffrey A. [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 1128 - 1133]

23
[ 79455-63-3 ]
[ 66073-54-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia In tetrahydrofuran; methanol

24
[ 66073-54-9 ]
[ 1370518-28-7 ]
[ 1370518-25-4 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In tetrahydrofuran for 23h; Inert atmosphere; Heating;

Reference： [1]Location in patent: experimental part Rörsch, Florian; Buscató, Estel.La; Deckmann, Klaus; Schneider, Gisbert; Schubert-Zsilavecz, Manfred; Geisslinger, Gerd; Proschak, Ewgenij; Grösch, Sabine [Journal of Medicinal Chemistry, 2012, vol. 55, # 8, p. 3792 - 3803]

25
[ 443-33-4 ]
[ 66073-54-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With [RuCl₂(η²-C₆H₆){P(NMe₂)₃}]; water at 100℃; for 3h; Inert atmosphere; Sealed tube;
80%	With [PdCl2{κ²-(P,N)-2-Ph2PC6H4CH=NOH}] In water at 100℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Garcia-Alvarez, Rocio; Diaz-Alvarez, Alba E.; Borge, Javier; Crochet, Pascale; Cadierno, Victorio [Organometallics, 2012, vol. 31, # 17, p. 6482 - 6490]
[2]Menéndez-Rodríguez, Lucía; Tomás-Mendivil, Eder; Francos, Javier; Nájera, Carmen; Crochet, Pascale; Cadierno, Victorio [Catalysis science and technology, 2015, vol. 5, # 7, p. 3754 - 3761]

26
[ 66073-54-9 ]
[ 1513851-25-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 1,2-dichloro-ethane / 24 h / Reflux 2.1: dichloromethane / 2 h / 20 °C 3.1: trifluoroacetic acid / 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran / 20 °C 4.1: water; sodium hydroxide / tetrahydrofuran / 3 h / 20 °C 5.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / tetrahydrofuran / 1 h / 20 °C 5.2: 15 h / 20 °C