957207-58-8|Methyl 4-bromo-2-(trifluoromethyl)benzoate| Ambeed

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Quality Control of [ 957207-58-8 ] Purity: 98% SDS Specification

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Product Details of [ 957207-58-8 ]

CAS No. :	957207-58-8
Formula :	C₉H₆BrF₃O₂
M.W :	283.04
SMILES Code :	COC(=O)C1=C(C=C(Br)C=C1)C(F)(F)F
MDL No. :	MFCD12761599
Boiling Point :	No data available
InChI Key :	PFBLWQAOLPCMIJ-UHFFFAOYSA-N
Pubchem ID :	46311087

Safety of [ 957207-58-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H227-H315-H319-H335
Precautionary Statements:	P305+P351+P338

Application In Synthesis of [ 957207-58-8 ]

* 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 [ 957207-58-8 ]

[ 957207-58-8 ] Synthesis Path-Downstream 1~27

1
[ 67-56-1 ]
[ 320-31-0 ]
[ 957207-58-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrogenchloride;Reflux;	H10) 4-Bromo-2-trifluoromethyl-benzoic acid methyl ester A solution of compound H9 (25.0 g, 94 mmol) in HCl-MeOH (250 mL) was refluxed overnight. TLC showed the starting material was consumed completely. The MeOH was evaporated in vacuo. And the resulting reside was partitioned between saturated NaHCO3 and EtOAc. The organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum to give product H10 (23.5 g; 90.0percent).
85%	With thionyl chloride; at 60℃; for 12.0h;	Synthesis of methyl 4-bromo-2-(trifluoromethyl)benzoate (107): 4-Bromo-2- (trifluoromethyl)benzoic acid (106; 1.6 g, 5.95 mmol) was dissolved in 20 mL of MeOH. 2 mL of SOd2 was added slowly. After the addition, the mixture was stirred at 60 °C for 12 h and concentrated. 20 mL of EtOAc was added to the residue. The mixture was washed with NaHCO3 aqueous solution, brine, dried over anhydrous Na2504 and concentrated to afford 1.6 g of methyl 4-bromo-2-(trifluoromethyl)benzoate 107 as yellow liquid. Yield (85percent). LCMS: m/z 282.7 [M+H], tR = 1.79 min
25.8 g	With thionyl chloride; at 0℃; for 18.0h;Reflux;	Example 222: 4,5-Dihydr6xy-2-(4-methyI-2-(trifluoromethyl)benzyI)isophthalonitrile Methyl 4-bromo-2-(trifltioromethyl)benzoate 4-Bromo-2-trifluoromethyl benzoic acid (25 g) was dissolved in methanol (300 ml) and cooled to 0 °C. Thionyl chloride (88.8 g) was added and the mixture was refluxed for 18 h. The reaction mixture was concentrated under vacuum. Yield 25.8 g 1H NMR (400 MHz, chloroform-d) ppm 7.89 (d, 7=1.6 Hz, 1 H) 7.75 (dd, 7=8.0, 1.6 Hz, 1 H) 7.68 (d, 7=8.0 Hz, 1 H) 3.93 (s, 3 H)

References: [1]Patent: US2012/28952,2012,A1 .Location in patent: Page/Page column 18-19.
[2]Patent: WO2017/31213,2017,A1 .Location in patent: Paragraph 00419.
[3]Patent: WO2013/175053,2013,A1 .Location in patent: Page/Page column 120-121.

2
[ 823-96-1 ]
[ 957207-58-8 ]
methyl 4-methyl-2-(trifluoromethyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12.4 g	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 120℃; for 18.0h;Inert atmosphere;	Methyl 4-methyI-2-(trifluoromethyl)benzoate Trimethylboroxine (16.2 g), tetrakis(triphenylphosphine)palladium(0) (8.2 g) and cesium carbonate (69.0 g) were added to a solution of methyl 4-brom0-2-(triflu6romethyl)benzoate (20.0 g) in 1 ,4-dioxane (500 ml) under argon atmosphere. The reaction mixture was heated at 120 °C for 18 h. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water, dried (Na2S04) and concentrated at 40 °C under vacuum. The crude product was purified by column chromatography. Yield 12.4 g NMR (400 MHz, chloroform-^ ppm 7.71 (d, 7=8.0 Hz, 1 H) 7.55 (s, 1 H) 7.40 (d, 7=8.0 Hz, 1 H) 3.92 (s, 3 H) 2.45 (s, 3 H) '

References: [1]Patent: WO2013/175053,2013,A1 .Location in patent: Page/Page column 121.

3
[ 191165-13-6 ]
[ 957207-58-8 ]

References: [1]Organic Letters,2015,vol. 17,p. 38 - 41.

4
[ 623-00-7 ]
[ 957207-58-8 ]

References: [1]Organic Letters,2015,vol. 17,p. 38 - 41.

5
[ 619-42-1 ]
[ 76-05-1 ]
[ 107317-58-8 ]
[ 957207-58-8 ]

References: [1]Organic Letters,2015,vol. 17,p. 38 - 41.

6
[ 186581-53-3 ]
[ 320-31-0 ]
[ 957207-58-8 ]

References: [1]Organic Letters,2015,vol. 17,p. 38 - 41.

7
[ 957207-58-8 ]
[ 411235-57-9 ]
methyl 4-cyclopropyl-2-(trifluoromethyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 20 - 110℃; for 7.0h;Inert atmosphere;	To a solution of <strong>[957207-58-8]methyl 4-bromo-2-(trifluoromethyl)benzoate</strong> (537 mg, 1.67 mmol) in 13 mL of toluene was added at room temperature cyclopropylboronic acid (220 mg, 2.56 mmol), K3PO4 (641 mg, 3.02 mmol), water (0.4 mL) and Pd(Ph3)4 (193 mg, 0.167 mmol) and the resulting mixture was degassed for 10 minutes with a stream of N2. The reaction mixture was stirred at 110 C for 7 hours. Water was added and product was extracted with ethyl acetate (three times). The collected organic layers were dried over Na2SO4, filtered and evaporated in high vacuum to yield methyl 4-cyclopropyl-2-(trifluoromethyl)benzoate (crude, 802 mg) as agrey solid. MS found for C12H11F3O2 as (M+H)+ 245.0.

References: [1]Patent: WO2016/196776,2016,A2 .Location in patent: Paragraph 00894.

8
[ 957207-58-8 ]
4-cyclopropyl-2-(trifluoromethyl)benzoic acid [ No CAS ]

References: [1]Patent: WO2016/196776,2016,A2 .

9
[ 957207-58-8 ]
(E)-3-(6-aminopyridin-3-yl)-N-((5-(4’-(3,3-difluoroazetidine-1-carbonyl)-3-(trifluoromethyl)-[1,1‘-biphenyl]-4-yl)-1,3,4-oxadiazol-2-yl)methyl)acrylamide [ No CAS ]

References: [1]Patent: WO2017/31213,2017,A1 .

10
[ 957207-58-8 ]
[ 1035928-56-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrazine hydrate; In ethanol; at 100℃; for 12.0h;	Synthesis of 4-bromo-2-(trifluoromethyl)benzohydrazide (108): Methyl 4-bromo- 2-(trifluoromethyl)benzoate (107; 1.6 g, 5.65 mmol) was dissolved in 20 mL of EtOH. 4 mL of hydrazine hydrate was added. The resulting mixture was stirred at 100 °C for 12 h, and concentrated to remove most of the solvent. The white precipitate was collected by filtration and dried under reduced pressure to yield 1.6 g of 4-bromo-2-(trifluoromethyl)benzohydrazide 108 as white solid. Yield (85percent). LCMS: m/z 284.7 [M+H], tR = 1.38 min

References: [1]Patent: WO2017/31213,2017,A1 .Location in patent: Paragraph 00420.

11
[ 957207-58-8 ]
benzyl 2-(2-(4-bromo-2-(trifluoromethyl)benzoyl)hydrazinyl)-2-oxoethylcarbamate [ No CAS ]

References: [1]Patent: WO2017/31213,2017,A1 .

12
[ 957207-58-8 ]
benzyl (5-(4-bromo-2-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2-yl)methylcarbamate [ No CAS ]

References: [1]Patent: WO2017/31213,2017,A1 .

13
[ 957207-58-8 ]
benzyl (5-(4’-(3,3-difluoroazetidine-1-carbonyl)-3-(trifluoromethyl)biphenyl-4-yl)-1,3,4-oxadiazol-2-yl)methylcarbamate [ No CAS ]

References: [1]Patent: WO2017/31213,2017,A1 .

14
[ 957207-58-8 ]
1-(4’-(5-(aminomethyl)-1,3,4-oxadiazol-2-yl)-3'-(trifluoromethyl)biphenyl-4-yl)(3,3-difluoroazetidin-1-yl)methanone [ No CAS ]

References: [1]Patent: WO2017/31213,2017,A1 .

15
[ 957207-58-8 ]
7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-5-carbonitrile [ No CAS ]
methyl 4-(5-cyanobenzofuran-7-yl)-2-(trifluoromethyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In water; N,N-dimethyl-formamide; at 90℃; for 0.5h;Inert atmosphere;	Methyl 4-bromo-2-(trifluoromethyl)benzoate (0.408 g, 1.44 mmol),7-(4,4,5, 5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzofuran-5-carbonitrile (0.353 g, 1.31 mmol),1,1 ?-bi s(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (53 mg,0.065 mmol) and N,N-dimethylformamide (8 mL) were added gradually to a 50 mL two-neckflask. A solution of potassium carbonate (1.3 mL, 2 M) in water was added under nitrogen, thenthe reaction mixture was stirred for 0.5 h at 90 °C. The resulting mixture was cooled to roomtemperature. To the resulting mixture was added saturated brine (80 mL). The mixture was extracted with ethyl acetate (40 mL x 2). The combined organic phase was washed with saturated brine (60 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (dichloromethane/petroleum ether (v/v) = 1/15) to give the title compound as a white solid (0.348 g, 77percent).MS (ES-API, pos. ion) m/z: 346.1 [M + 1]t

References: [1]Patent: WO2017/36404,2017,A1 .Location in patent: Page/Page column 109; 110.

16
[ 80-73-9 ]
[ 957207-58-8 ]
[ 257610-49-4 ]
methyl 4-(1-fluorovinyl)-2-(trifluoromethyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine)palladium (0);	Example 6 Preparation of methyl 4-(1-fluorovinyl)-2-(trifluoromethyl)benzoate (C28) To a 100 mL round-bottomed flask was added <strong>[957207-58-8]methyl 4-bromo-2-(trifluoromethyl)benzoate</strong> (2.25 g, 8.00 mmol), (1-fluorovinyl)(methyl)diphenylsilane (3.58 g, 14.8 mmol), and 1,3-dimethylimidazolidin-2-one (40 mL). Tetrakis(triphenylphosphine)palladium(0) (0.459 g, 0.400 mmol), copper(I) iodide (0.0760 mg, 0.400 mmol), and cesium fluoride (3.62 g, 23.9 mmol) were added and the reaction was stirred at room temperature for 24 hours under a nitrogen atmosphere. Water was added to the mixture and the mixture was diluted with 3:1 hexanes/diethyl ether. The layer was separated, and the organic layer was dried over sodium sulfate, concentrated, and the residue was purified by flash column chromatography provided the title compound as a colorless oil (2.00 g, 96percent): 1H NMR (400 MHz, CDCl3) delta 7.96-7.87 (m, 1H), 7.83 (dq, J=8.1, 0.7 Hz, 1H), 7.77 (dd, J=8.2, 1.7 Hz, 1H), 5.23 (dd, J=48.6, 4.0 Hz, 1H), 5.07 (dd, J=17.4, 4.0 Hz, 1H), 3.95 (s, 3H); 19F NMR (376 MHz, CDCl3) delta -59.92, -108.73 (d, J=1.4 Hz); EIMS m/z 248 ([M]+).

References: [1]Patent: US2017/208803,2017,A1 .

17
[ 957207-58-8 ]
[ 257610-49-4 ]
methyl 4-(1-fluorovinyl)-2-(trifluoromethyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride; at 20 - 24℃; for 24.0h;Inert atmosphere;	To a 100 mL round-bottomed flask was added <strong>[957207-58-8]methyl 4-bromo-2-(trifluoromethyl)benzoate</strong> (2.25 g, 8.00 mmol), fluorovinyl) (methyl)diphenylsilane (3.58 g, 14.8 mmol), and 1,3-dimethylimidazolidin-2-one (40 mL). Tetrakis(triphenylphosphine)palladium(0) (0.459 g, 0.400 mmol), copper(I) iodide (0.0760 mg, 0.400 mmol), and cesium fluoride (3.62 g, 23.9 mmol) were added and the reaction was stirred at room temperature for 24 hours under a nitrogen atmosphere. Water was added to the mixture and the mixture was diluted with 3:1 hexanes/diethyl ether. The layer was separated, and the organic layer was dried over sodium sulfate, concentrated, and the residue was purified by flash column chromatography provided the title compound as a colorless oil (2.00 g, 96percent): 1H NMR (400 MHz, CDCl3) delta 7.96-7.87 (m, 1H), 7.83 (dq, J=8.1, 0.7 Hz, 1H), 7.77 (dd, J=8.2, 1.7 Hz, 1H), 5.23 (dd, J=48.6, 4.0 Hz, 1H), 5.07 (dd, J=17.4, 4.0 Hz, 1H), 3.95 (s, 3H); 19F NMR (376 MHz, CDCl3) delta?59.92, ?108.73 (d, J=1.4 Hz); EIMS m/z 248 ([M]+)
96%	With 1,3-dimethyl-2-imidazolidinone; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride; at 20℃; for 24.0h;Inert atmosphere;	Example 6 Preparation of methyl 4-(1-fluorovinyl)-2-(trifluoromethyl)benzoate (C28) To a 100 mL round-bottomed flask was added <strong>[957207-58-8]methyl 4-bromo-2-(trifluoromethyl)benzoate</strong> (2.25 g, 8.00 mmol), (1-fluorovinyl)(methyl)diphenylsilane (3.58 g, 14.8 mmol), and 1,3-dimethylimidazolidin-2-one (40 mL). Tetrakis(triphenylphosphine)palladium(0) (0.459 g, 0.400 mmol), copper(I) iodide (0.0760 mg, 0.400 mmol), and cesium fluoride (3.62 g, 23.9 mmol) were added and the reaction was stirred at room temperature for 24 hours under a nitrogen atmosphere. Water was added to the mixture and the mixture was diluted with 3:1 hexanes/diethyl ether. The layer was separated, and the organic layer was dried over sodium sulfate, concentrated, and the residue was purified by flash column chromatography provided the title compound as a colorless oil (2.00 g, 96percent): 1H NMR (400 MHz, CDCl3) delta 7.96-7.87 (m, 1H), 7.83 (dq, J=8.1, 0.7 Hz, 1H), 7.77 (dd, J=8.2, 1.7 Hz, 1H), 5.23 (dd, J=48.6, 4.0 Hz, 1H), 5.07 (dd, J=17.4, 4.0 Hz, 1H), 3.95 (s, 3H); 19F NMR (376 MHz, CDCl3) delta -59.92, -108.73 (d, J=1.4 Hz); EIMS m/z 248 ([M]+).
96%	With 1,3-dimethyl-2-imidazolidinone; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride; at 20 - 24℃; for 24.0h;Inert atmosphere;	Example 6: Preparation of methyl 4-(1-fluorovinyl)-2-(trifluoromethyl)benzoate (C28) (0215) (0216) To a 100 mL round-bottomed flask was added 90 <strong>[957207-58-8]methyl 4-bromo-2-(trifluoromethyl)benzoate</strong> (2.25 g, 8.00 mmol), 91 (1-fluorovinyl)(methyl)diphenylsilane (3.58 g, 14.8 mmol), and 92 1,3-dimethylimidazolidin-2-one (40 mL). 65 Tetrakis(triphenylphosphine)palladium(0) (0.459 g, 0.400 mmol), 59 copper(I) iodide (0.0760 mg, 0.400 mmol), and 93 cesium fluoride (3.62 g, 23.9 mmol) were added and the reaction was stirred at room temperature for 24 hours under a nitrogen atmosphere. 70 Water was added to the mixture and the mixture was diluted with 3:1 hexanes/diethyl ether. The layer was separated, and the organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash column chromatography provided the 94 title compound as a colorless oil (2.00 g, 96percent): 1H NMR (400 MHz, CDCl3) delta 7.96-7.87 (m, 1H), 7.83 (dq, J=8.1, 0.7 Hz, 1H), 7.77 (dd, J=8.2, 1.7 Hz, 1H), 5.23 (dd, J=48.6, 4.0 Hz, 1H), 5.07 (dd, J=17.4, 4.0 Hz, 1H), 3.95 (s, 3H); 19F NMR (376 MHz, CDCl3) delta ?59.92, ?108.73 (d, J=1.4 Hz); EIMS m/z 248 ([M]+).

96%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride; at 20 - 24℃; for 24.0h;Inert atmosphere;	Preparation of methyl 4-(1-fluorovinyl)-2-(trifluoromethyl)benzoate (C28) To a 100 mL round-bottomed flask was added <strong>[957207-58-8]methyl 4-bromo-2-(trifluoromethyl)benzoate</strong> (2.25 g, 8.00 mmol), (1-fluorovinyl)(methyl)diphenylsilane (3.58 g, 14.8 mmol), and 1,3-dimethylimidazolidin-2-one (40 mL). Tetrakis(triphenylphosphine)palladium(0) (0.459 g, 0.400 mmol), copper(I) iodide (0.0760 mg, 0.400 mmol), and cesium fluoride (3.62 g, 23.9 mmol) were added and the reaction was stirred at room temperature for 24 hours under a nitrogen atmosphere. Water was added to the mixture and the mixture was diluted with 3:1 hexanes/diethyl ether. The layer was separated, and the organic layer was dried over sodium sulfate, concentrated, and the residue was purified by flash column chromatography provided the title compound as a colorless oil (2.00 g, 96percent): 1H NMR (400 MHz, CDCl3) delta 7.96-7.87 (m, 1H), 7.83 (dq, J=8.1, 0.7 Hz, 1H), 7.77 (dd, J=8.2, 1.7 Hz, 1H), 5.23 (dd, J=48.6, 4.0 Hz, 1H), 5.07 (dd, J=17.4, 4.0 Hz, 1H), 3.95 (s, 3H); 19F NMR (376 MHz, CDCl3) delta -59.92, -108.73 (d, J=1.4 Hz); EIMS m/z 248 ([M]+).
96%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride; at 20 - 24℃; for 24.0h;Inert atmosphere;	Example 6 Preparation of methyl 4-(1-fluorovinyl)-2-(trifluoromethyl)benzoate (C38) To a 100 mL round-bottomed flask was added <strong>[957207-58-8]methyl 4-bromo-2-(trifluoromethyl)benzoate</strong> (2.25 g, 8.00 mmol), (1-fluorovinyl)(methyl)diphenylsilane (3.58 g, 14.8 mmol), and 1,3-dimethylimidazolidin-2-one (40 mL). Tetrakis(triphenylphosphine)palladium(0) (0.459 g, 0.400 mmol), copper(I) iodide (0.0760 mg, 0.400 mmol), and cesium fluoride (3.62 g, 23.9 mmol) were added and the reaction mixture was stirred at room temperature for 24 hours under a nitrogen atmosphere. Water was added to the mixture and the mixture was diluted with 3:1 hexanes/diethyl ether. The organic layer was dried over sodium sulfate, filtered and concentrated. Purification by flash column chromatography provided the title compound as a colorless oil (2.00 g, 96percent): 1H NMR (400 MHz, CDCl3) delta 7.96-7.87 (m, 1H), 7.83 (dq, J=8.1, 0.7 Hz, 1H), 7.77 (dd, J=8.2, 1.7 Hz, 1H), 5.23 (dd, J=48.6, 4.0 Hz, 1H), 5.07 (dd, J=17.4, 4.0 Hz, 1H), 3.95 (s, 3H); 19F NMR (376 MHz, CDCl3) delta -59.92, -108.73 (d, J=1.4 Hz); EIMS m/z 248 ([M]+).

References: [1]Patent: US2017/208804,2017,A1 .Location in patent: Paragraph 0234; 0235.
[2]Patent: US2017/208810,2017,A1 .Location in patent: Paragraph 0213-0214.
[3]Patent: US2017/208806,2017,A1 .Location in patent: Paragraph 0215; 0216.
[4]Patent: US2017/208805,2017,A1 .Location in patent: Paragraph 0209-0210.
[5]Patent: US2018/279612,2018,A1 .Location in patent: Paragraph 0308-0309.

18
[ 957207-58-8 ]
(Z)-4-(1-ethoxy-4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)-2-(trifluoromethyl)benzoic acid [ No CAS ]