[ CAS No. 367-23-7 ] {[proInfo.proName]}

Name: 367-23-7|1,2,4-Trifluorobenzene|98%
Brand: Ambeed
SKU: A859089
Rating: 93 (28 reviews)

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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 367-23-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 367-23-7 ]

Product Details of [ 367-23-7 ]

CAS No. :	367-23-7	MDL No. :	MFCD00000305
Formula :	C₆H₃F₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PEBWOGPSYUIOBP-UHFFFAOYSA-N
M.W :	132.08	Pubchem ID :	67773
Synonyms :

Calculated chemistry of [ 367-23-7 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	26.32
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.84
Log Po/w (XLOGP3) :	2.52
Log Po/w (WLOGP) :	3.36
Log Po/w (MLOGP) :	3.58
Log Po/w (SILICOS-IT) :	3.13
Consensus Log Po/w :	2.89

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.74
Solubility :	0.24 mg/ml ; 0.00182 mol/l
Class :	Soluble
Log S (Ali) :	-2.17
Solubility :	0.901 mg/ml ; 0.00682 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.2
Solubility :	0.0835 mg/ml ; 0.000632 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.23

Safety of [ 367-23-7 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P233-P235-P240-P241-P242-P243-P260-P261-P264-P271-P280-P302+P352-P303+P361+P353-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P370+P378-P403-P403+P233-P403+P235-P405-P501	UN#:	1993
Hazard Statements:	H225-H315-H319-H335	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 367-23-7 ]

* 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.

Upstream synthesis route of [ 367-23-7 ]
Downstream synthetic route of [ 367-23-7 ]

[ 367-23-7 ] Synthesis Path-Upstream 1~8

1
[ 367-23-7 ]
[ 2991-28-8 ]

Reference： [1] Journal of Physical Chemistry A, 2000, vol. 104, # 2, p. 352 - 361

2
[ 367-23-7 ]
[ 327-52-6 ]

Yield	Reaction Conditions	Operation in experiment
98.7%	at 20℃; for 2 h;	To a 500-mL three-necked flask, 100 g of 1,2,4-trifluorobenzene and 3 g of tin tetrachloride-polystyrene composite were added. Glacial acetic acid was used as a reaction solvent. 127 mL of liquid bromine was slowly added dropwise at room temperature. Reaction 2h, TLC monitoring raw material reaction is complete, vacuum evaporate glacial acetic acid, add 500mL of chloroform, and then wash the organic phase with a concentration of 3percent diluted hydrochloric acid, add saturated sodium sulfite solution to remove the bromine in the organic phase, and wash sequentially, After washing with saturated saline and distilling off the solvent, 158 g of the product, trifluorobromobenzene, was obtained in a yield of 98.7percent, and the purity by gas chromatography was 99.6percent.

Reference： [1] Patent: CN107673951, 2018, A, . Location in patent: Paragraph 0015; 0016; 0017; 0018
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 153[3] Journal of the American Chemical Society, 1959, vol. 81, p. 94,98

3
[ 540-36-3 ]
[ 367-23-7 ]
[ 2713-31-7 ]
[ 703-16-2 ]
[ 22060-77-1 ]

Reference： [1] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 11, p. 1807 - 1811

4
[ 367-23-7 ]
[ 17533-08-3 ]

Reference： [1] Nucleosides, Nucleotides and Nucleic Acids, 2001, vol. 20, # 1-2, p. 11 - 40
[2] Australian Journal of Chemistry, 1979, vol. 32, p. 737 - 753

5
[ 367-23-7 ]
[ 66684-57-9 ]

Reference： [1] Journal of Organic Chemistry, 1995, vol. 60, # 22, p. 7348 - 7350

6
[ 367-23-7 ]
[ 2105-61-5 ]

Reference： [1] Chemische Berichte, 1951, vol. 84, p. 101,108
[2] Journal of the American Chemical Society, 1951, vol. 73, p. 153[3] Journal of the American Chemical Society, 1959, vol. 81, p. 94,98

7
[ 124-38-9 ]
[ 367-23-7 ]
[ 2358-29-4 ]

Reference： [1] Journal of the American Chemical Society, 2010, vol. 132, # 26, p. 8858 - 8859
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 46, p. 8674 - 8677
[3] Journal of Physical Chemistry A, 2000, vol. 104, # 2, p. 352 - 361

8
[ 367-23-7 ]
[ 98349-24-7 ]

Reference： [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 1, p. 168 - 174

[ 367-23-7 ] Synthesis Path-Downstream 1~69

1
[ 367-23-7 ]
[ 327-52-6 ]

Yield	Reaction Conditions	Operation in experiment
98.7%	With bromine; acetic acid; at 20℃; for 2h;	To a 500-mL three-necked flask, 100 g of 1,2,4-trifluorobenzene and 3 g of tin tetrachloride-polystyrene composite were added. Glacial acetic acid was used as a reaction solvent. 127 mL of liquid bromine was slowly added dropwise at room temperature. Reaction 2h, TLC monitoring raw material reaction is complete, vacuum evaporate glacial acetic acid, add 500mL of chloroform, and then wash the organic phase with a concentration of 3% diluted hydrochloric acid, add saturated sodium sulfite solution to remove the bromine in the organic phase, and wash sequentially, After washing with saturated saline and distilling off the solvent, 158 g of the product, trifluorobromobenzene, was obtained in a yield of 98.7%, and the purity by gas chromatography was 99.6%.

Reference： [1]Patent: CN107673951,2018,A .Location in patent: Paragraph 0015; 0016; 0017; 0018
[2]Journal of the American Chemical Society,1951,vol. 73,p. 153
Journal of the American Chemical Society,1959,vol. 81,p. 94,98

2
[ 367-23-7 ]
[ 75-36-5 ]
[ 129322-83-4 ]

Reference： [1]Organic Preparations and Procedures International,1991,vol. 23,p. 655 - 658
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 168 - 174
[3]Journal of Physical Chemistry A,2000,vol. 104,p. 352 - 361

3
[ 367-23-7 ]
[ 17533-08-3 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2001,vol. 20,p. 11 - 40
[2]Australian Journal of Chemistry,1979,vol. 32,p. 737 - 753

4
[ 367-23-7 ]
[ 66684-57-9 ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 7348 - 7350

5
[ 10576-12-2 ]
[ 367-23-7 ]
N-(2,4-Difluoro-phenoxy)-acetimidic acid ethyl ester [ No CAS ]

Reference： [1]Organic Preparations and Procedures International,1997,vol. 29,p. 594 - 600

6
[ 455-17-4 ]
[ 540-36-3 ]
[ 367-23-7 ]
[ 75186-45-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 4 % Chromat. 2: 3 % Chromat. 3: 24 % Chromat.	With boron trifluoride methanol complex; fluorine In methanol; dichloromethane; trichlorofluoromethane at -78℃; for 5h; Title compound not separated from byproducts;
	With fluorine In methanol at -78℃; for 5h; other co-solvents, also in the presence of protic and Lewis acid as catalyst;

Reference： [1]Stuart, Alison M.; Coe, Paul L.; Moody, David J. [Journal of Fluorine Chemistry, 1998, vol. 88, # 2, p. 179 - 184]
[2]Stuart, Alison M.; Coe, Paul L.; Moody, David J. [Journal of Fluorine Chemistry, 1998, vol. 88, # 2, p. 179 - 184]

7
[ 367-23-7 ]
[ 79-04-9 ]
[ 129604-31-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With aluminium trichloride
93%	With aluminum (III) chloride at 70℃; for 16h;	1 Synthesis of 2-Chloro-1-(2,4,5-trifluorophenyl)ethanone of formula VII-X=Cl Synthesis of 2-Chloro-1-(2,4,5-trifluorophenyl)ethanone of formula VII-X=Cl 10051] A mixture of 1,2,4-trifluorobenzene (15 ml, 144mmol) of formula (VIII), chloroacetyl chloride (11.5 ml, 145mmol) and aluminium trichloride (38.3 g, 285 mmol) wasstirred at 70°C. for 16 h. It was then neutralised with aqueoussaturated Na2CO3. The resulting mixture was extracted withEt20 (3x30 ml) and the combined organic phases werewashed with an aqueous solution of NaHCO3 (30 ml) andbrine (30 ml), then dried with Mg504 and concentrated in therotary evaporatot The residue was thrther purified by sublimation obtaining 27.1 g of colourless crystalline product witha molar yield of 93%.
	In ice-water; dichloromethane	1 2,4,5-Trifluoro-α-chloroacetophenone EXAMPLE 1 2,4,5-Trifluoro-α-chloroacetophenone 239 g (179 mol) of aluminium chloride are introduced into 99 g (0.75 mol) of 1,2,4-trifluorobenzene at 20° C. 130 g of chloroacetyl chloride (1.15 mol) are metered into the suspension at 60° C. with stirring in the course of 2 hours. The mixture is allowed to react further at 80° C. for 1 h and the liquid reaction product is then poured into 1 l of ice-water. The reaction product is extracted from the aqueous phase 3 times using a total of 300 ml of dichloromethane. The combined organic phases are dried over magnesium oxide and evaporated. The solid crude product is then distilled through a Vigreux column (b.p.: 104° C., 20 mbar). 139 g of solid 2,4,5-trifluoro-α-chloroacetophenone are obtained, which corresponds to 89% of theory, relative to 1,2,4-trifluorobenzene.

Reference： [1]Braish, Tamim F.; Fox, Darrell E. [Organic Preparations and Procedures International, 1991, vol. 23, # 5, p. 655 - 658]
[2]Current Patent Assignee: HOLDING F.I.S. S.P.A. - US2014/58126, 2014, A1 Location in patent: Paragraph 0050; 0051
[3]Current Patent Assignee: SANOFI; HONEYWELL INTERNATIONAL INC - US5093529, 1992, A

8
[ 124-38-9 ]
[ 367-23-7 ]
[ 2358-29-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: carbon dioxide With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); potassium hydroxide In tetrahydrofuran at 20℃; for 0.25h; Stage #2: 1,2,4-trifluorobenzene In tetrahydrofuran at 20℃; for 12h; Stage #3: With hydrogenchloride In tetrahydrofuran; water regioselective reaction;
85%	Stage #1: carbon dioxide; 1,2,4-trifluorobenzene With cesium hydroxide; (hydroxido){N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene}copper(I) In tetrahydrofuran at 65℃; for 8h; Inert atmosphere; Stage #2: With hydrogenchloride In water Inert atmosphere; regioselective reaction;
	Stage #1: 1,2,4-trifluorobenzene With n-butyllithium In tetrahydrofuran at -70℃; Stage #2: carbon dioxide In tetrahydrofuran

Reference： [1]Boogaerts, Ine I. F.; Nolan, Steven P. [Journal of the American Chemical Society, 2010, vol. 132, # 26, p. 8858 - 8859]
[2]Boogaerts, Ine I. F.; Fortman, George C.; Furst, Marc R. L.; Cazin, Catherine S. J.; Nolan, Steven P. [Angewandte Chemie - International Edition, 2010, vol. 49, # 46, p. 8674 - 8677]
[3]Konovalov, Valery V.; Laev, Sergey S.; Beregovaya, Irina V.; Shchegoleva, Lyudmila N.; Shteingarts, Vitalij D.; Tsvetkov, Yuri D.; Bilkis, Itzhak [Journal of Physical Chemistry A, 2000, vol. 104, # 2, p. 352 - 361]

9
[ 367-23-7 ]
[ 2991-28-8 ]

Reference： [1]Journal of Physical Chemistry A,2000,vol. 104,p. 352 - 361

10
[ 367-23-7 ]
[ 85068-27-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaH, NMP / 2.) from 110 deg C to 115 deg C, 30 h 2: 93 percent / aq. NaOH / 18 h / 95 - 100 °C

Reference： [1]Kowalczyk, Bruce A. [Synthesis, 1997, # 12, p. 1411 - 1414]

11
[ 827-13-4 ]
[ 827-12-3 ]
[ 319-88-0 ]
[ 1489-53-8 ]
[ 372-38-3 ]
[ 367-23-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; sodium acetate In water at 140℃; for 6h;

Reference： [1]Current Patent Assignee: BASF SE - WO2006/111583, 2006, A1 Location in patent: Page/Page column 11-12

12
[ 446-17-3 ]
[ 367-23-7 ]

Yield	Reaction Conditions	Operation in experiment
94.9%	With ammonia; copper; In water; at 260℃; for 1.25h;	In the 500mL intermittent high pressure reaction kettle 300 g aqueous ammonia solution with ammonia concentration of 2 g / L, 60. 0g <strong>[446-17-3]2, 4, 5-trifluorobenzoic acid</strong> and 2. 00g copper powder, stir, The temperature was raised to 260 C decarboxylation reaction for 1.25 h. After decarboxylation reaction was completed, Open the exhaust valve pressure relief, recovery of ammonia inside the kettle; cooling to room temperature, The catalyst was recovered by filtration, and the filtrate was allowed to stand under the liquid-liquid layer to obtain the organic phase and the aqueous phase. After the organic phase was distilled, 1,2,4-trifluorobenzene 42. 7 g, The product was analyzed by HPLC for purity 98.9%, the yield was 94.9%.
	In quinoline;	EXAMPLE 1 Preparation of 1,2,4-trifluorobenzene from <strong>[446-17-3]2,4,5-trifluorobenzoic acid</strong> in quinoline After 1.0 g (0.0057 mol) of <strong>[446-17-3]2,4,5-trifluorobenzoic acid</strong>, 0.11 g of copper (II) oxide and 10 mL of quinoline were placed in a reaction vessel, the contents were heated under a nitrogen atmosphere at 200 C., at which time the reaction started effervescing. After heating at this temperature for 0.5 h, the reaction was cooled, and an internal standard added. 19 F NMR analysis of the reaction mixture indicated 0.6 g (80%) of 1,2,4-trifluorobenzene was formed.

Reference： [1]Patent: CN105732302,2016,A .Location in patent: Paragraph 0039; 0040
[2]Patent: US992,1991,H1

13
[ 79-36-7 ]
[ 367-23-7 ]
[ 375369-29-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: dichloroacethyl chloride; 1,2,4-trifluorobenzene at 60℃; Stage #2: With sodium hydroxide; water at 60℃; Stage #3: With hydrogenchloride In water at 0 - 20℃;	1 Example 1: 2, 4 , 5-Trifluoromandelic acid 5 (Z = COOH) Under inert atmosphere, 200 g aluminium trichloride in 100 g 1,2,4-trifluorobenzene is suspended, the mixture is heated to 60° C, and 167 g di-chloroacetyl chloride is added dropwise. Once the conversion is completed (GC) , the mixture is cooled to room temperature and it is taken up again with methylene chloride and water. The layers are separated and the organic layer is concentrated in vacuum. The reaction raw-material is then added dropwise on a mixture of 900 mL water and 90 g sodium hydroxide at 60° C. Once the conversion is completed, the mixture is cooled to room temperature, it is filtered and acidified with concentrated hydrochloric acid to pH = 1. The suspension is cooled to 0° C and it is filtered, isolating 130 g (84%) of product as a white solid with 98% HPLC purity (A%) . 1H-NMR (300 MHz, DMSO-d6) : δ (ppm) 3.92 (bs, IH); 4.85 (s, IH); 7.4-7.6 (m, 2H); 12.9 (bs, IH).

Reference： [1]Current Patent Assignee: HOLDING F.I.S. S.P.A. - WO2008/78350, 2008, A2 Location in patent: Page/Page column 13-14

14
[ 367-23-7 ]
[ 5008-19-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; bis(2,2,6,6-tetramethylpiperidinyl)zinc, lithium chloride, magnesium chloride complex; oxygen; manganese(ll) chloride In tetrahydrofuran at 20℃; for 1h;

Reference： [1]Truong, Thanh; Alvarado, Joseph; Tran, Ly Dieu; Daugulis, Olafs [Organic Letters, 2010, vol. 12, # 6, p. 1200 - 1203]

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[ 69550-28-3 ]
[ 367-23-7 ]
[ 1224321-78-1 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 5580 - 5581

16
[ 120-82-1 ]
[ 367-23-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium fluoride; C₆H₁₁BO₃ In sulfolane (tetramethylene sulfone) at 245℃; for 3h; Inert atmosphere;	31 EXAMPLE 31 20 g of potassium fluoride and 3.25 g of the IB-2 complex, the B/F ratio being 1/15, are added to 20 g of commercially available 1,2,4-trichlorobenzene in 70 ml of sulfolane (tetramethylene sulfone). The mixture is introduced into a Parr reactor which is sealed after sparging and flushing with nitrogen, and then brought to 245° C. and maintained at this temperature for 3 hours. The reactor is then cooled to normal temperature and, after opening, the reaction products are filtered. 24.2 g of KCl are obtained. The filtrate is extracted with 5×30 ml of pentane, which is immiscible with sulfolane, the aliquot parts are mixed and the solvent is evaporated off under reduced pressure. 10.5 g (78% yield) of 1,2,4-trifluorobenzene (Bp=90° C.) are obtained.

Reference： [1]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITY OF PICARDIE JULES VERNE - US2011/171112, 2011, A1 Location in patent: Page/Page column 23

17
[ 367-23-7 ]
[ 142055-44-5 ]
[ 1374967-00-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,2,4-trifluorobenzene; (S)-4-Carboxymethyl-5-oxo-oxazolidine-3-carboxylic acid methyl ester In dichloromethane at 20℃; for 5h; Inert atmosphere; Stage #2: With water In dichloromethane Cooling with ice;	2 Example 2(3R)-3-methoxycarbonylamino-4-(2,4,5-trifluorophenyl)-butyric acid (IIb)In inert atmosphere to a solution of compound IVa (21 g) in methylenechloride (50 ml) 1,2,4-trifluorobenzene Vb (26 g) was added, followed by slow addition of AlCl3 (35 g) in small portions at rt under good stirring. The slurry was stirred at rt for ca. 5 hrs until the reaction was completed and no IVa was present (TLC), then carefully poured on ice (400 g) and the water phase extracted 3 times with methylenechloride (3×100 ml), the combined organic phases dried over sodium sulfate, filtered and evaporated under vacuum to give the crude compound IIIb as yellow oil: 22 g (73% yield) which was immediately used for reduction step.To a solution of crude compound IIIb (22 g) in methanol (100 ml), after addition of conc.-HCl (1 ml) and 10% Pd-C (500 mg), the reaction mixture was hydrogenated at rt under vigorous stirring and slightly elevated hydrogen-pressure (4 bar) until the starting compound IIIb completely disappeared (5 hrs, TLC). After filtration of the catalyst, the filtrate was concentrated under vacuum to provide the title compound IIb as a yellow solid: 19.3 g (66% yield calc. from IVa) which was recrystallized from hot TBME/ethanol mixture providing pure title compound with 99.1% ee. Anal. calculated for C12H12F3NO4: C, 49.49; H, 4.15; F, 19.57; N, 4.81; O, 21.98. Found: C, 49.39; H, 4.25; F, 19.37; N, 4.71; O 22.18.

Reference： [1]Current Patent Assignee: DRUG PROCESS LICENSING ASSOCIATES, LLC - US2012/123144, 2012, A1 Location in patent: Page/Page column 5

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[ 367-23-7 ]
[ 21933-62-0 ]
[ 1374967-01-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1,2,4-trifluorobenzene; (S)-4-Methoxycarbonylmethyloxazolidin-2,5-dione In dichloromethane at 30℃; for 5h; Inert atmosphere; Stage #2: With water In dichloromethane Cooling with ice;	3 Example 3(3R)-3-amino-4-(2,4,5-trifluorophenyl)-butyric acid methyl ester hydrochloride (IIc)In inert atmosphere to a cooled solution of compound (IVc, 17.3 g) and 1,2,4-trifluorobenzene (75 g) in methylenechloride (100 ml) under vigorous stirring slowly in small portions AlCl3 (46 g) was added that the reaction temperature did not exceed 30° C. After stirring for 5 hrs at it the slurry was poured onto ice (250 g), the aqueous phase extracted 3 times with methylenechloride (3×200 ml), the combined organic phase dried over magnesium sulfate (100 g), filtered and evaporated under reduced pressure to give hydrochloride of the compound IIIc as a yellow semi crystalline oil: 25 g (84% yield calc. to IVc) which was immediately subjected to reduction step.Crude compound (IIIc, 25 g) was dissolved in methanol (200 ml) and after addition of 10% Pd-C (500 mg) the reaction mixture was hydrogenated at it under stirring and slightly elevated hydrogen-pressure (4 bar) until the starting compound IIIc completely disappeared (ca. 4 hrs, TLC). After filtration of the catalyst the filtrate was concentrated under reduced pressure to provide the title compound IIc as a yellow solid: 20.2 g (71% yield calc. from IVc) which was recrystallized from hot toluene/methanol mixture providing the title compound II c with 98% ee. Anal. calculated for C11H13ClF3NO2: C, 46.57; H, 4.62; Cl, 12.50; F, 20.09; N, 4.94; O, 11.28. Found: C, 46.32; H, 4.80; Cl, 12.52; F, 20.19; N, 5.12; O, 11.32. The analytical data of IIc have been corresponding to data reported in Tetrahedron Asymmetry 2006, 17, 205.

Reference： [1]Current Patent Assignee: DRUG PROCESS LICENSING ASSOCIATES, LLC - US2012/123144, 2012, A1 Location in patent: Page/Page column 5-6

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[ 32362-99-5 ]
[ 367-23-7 ]
[ 1376608-77-3 ]