1003879-02-4|2-Bromo-1-(4-bromo-3-fluorophenyl)ethanone| Ambeed

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Quality Control of [ 1003879-02-4 ] Purity: 97% SDS Specification

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Product Details of [ 1003879-02-4 ]

CAS No. :	1003879-02-4
Formula :	C₈H₅Br₂FO
M.W :	295.93
SMILES Code :	FC1=C(Br)C=CC(=C1)C(=O)CBr
MDL No. :	MFCD11847180
InChI Key :	IELTVOHIKAUZFA-UHFFFAOYSA-N
Pubchem ID :	53416614

Safety of [ 1003879-02-4 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H314
Precautionary Statements:	P280-P305+P351+P338-P310
Class:	8
UN#:	3261
Packing Group:	Ⅲ

Application In Synthesis of [ 1003879-02-4 ]

* 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 [ 1003879-02-4 ]

[ 1003879-02-4 ] Synthesis Path-Downstream 1~26

Yield	Reaction Conditions	Operation in experiment
	With bromine; In acetic acid; at 50℃; for 1.5h;	General procedure: F) 2-bromo-1-(3-fluoro-4-(trifluoromethoxy)phenyl)ethanone To a solution of 1-(3-fluoro-4-(trifluoromethoxy)phenyl)ethanone (4.51 g) in acetic acid (50 mL) was slowly added a solution of bromine (1.12 mL) in acetic acid (5 mL) at room temperature. The reaction mixture was stirred at 50C for 1.5 hr, and the solvent was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (6.01 g). 1H NMR (300 MHz, DMSO-d6) δ 4.99 (2H, s), 7.73-7.84 (1H, m), 7.92-8.00 (1H, m), 8.12 (1H, dd, J = 11.0, 2.0 Hz).

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[ 153556-42-4 ]
[ 1003879-02-4 ]

References: [1]Patent: US2012/129832,2012,A1 .
[2]Patent: US2017/253614,2017,A1 .
[3]Patent: WO2012/48421,2012,A1 .

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References: [1]Patent: WO2012/48421,2012,A1 .
[2]Patent: US2017/253614,2017,A1 .

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[ 304445-49-6 ]
[ 1003879-02-4 ]

Yield	Reaction Conditions	Operation in experiment
44%	With copper(ll) bromide; In ethyl acetate; at 60℃; for 12h;	A mixture of 1-(4-bromo-3-fluorophenyl)ethanone (1 g, 4.6 mmol), copper(II) bromide (2.1 g, 9.7 mmol) in EtOAc (50 mL) was stirred for 12 hours at 60 C. The mixture was allowed to cool down and filtered. The filtrate was concentrated. The residue was chromatographed (silica, ethyl acetate/petroleum ether) to give the desired compound as a yellow solid (600 mg, 44%).
	With phenyltrimethylammonium tribromide; In tetrahydrofuran; at 20℃; for 1h;	Step 3:; To a stirred solution of 1a3 (9.8 g, 45.3 mmol) in THF (90 mL) is added portionwise phenyltrimethylammonium tribromide (17.0 g, 45.3 mmol). The reaction mixture is stirred for 1 h at RT. Water is added, followed by EtOAc and the layers are separated. The organic layer is washed with water, brine, dried over MgS04, filtered and concentrated. The product is purified by flash chromatography using 100% hexanes to afford 1a4.
	With copper(ll) bromide; In ethyl acetate; at 60℃; for 4h;	A solution of compound 4-1 (0.5 g, 2.3 mmol) and CuBr2 (1.13 g, 4.84 mmol) in EtOAc (5.0 mL) was stirred at 60 C for 4 hrs. After the reaction was completed, the mixture was cooled to rt and filtered. 20 mL of water was added to the filtrate and the resulting mixture was extracted with EtOAc (50 mL x 3). The combined organic layers were dried over anhydrous Na2S04 and concentrated in vacuo to give the title compound as a yellow solid (0.78 g). which was used for the next step without further purification.

0.78 g	With copper(ll) bromide; In ethyl acetate; at 60℃; for 4h;	10839] A solution of compound 4-1 (0.5 g, 2.3 mmol) and Cu13r2 (1.13 g, 4.84 mmol) in EtOAc (5.0 mE) was stirred at 60C. for 4 hrs. After the reaction was completed, the mixture was cooled tort and filtered. 20 mE of water was added to the filtrate and the resulting mixture was extracted with EtOAc (50 mEx3). The combined organic layers were dried over anhydrous Na2504 and concentrated in vacuo to give the title compound as a yellow solid (0.78 g), which was used for the next step without thrther purification.
3.58 g	With phenyltrimethylammonium tribromide; In tetrahydrofuran; at 0 - 35℃; for 48h;	A) 2-bromo-1-(4-bromo-3-fluorophenyl)ethanone To a solution of 1-(4-bromo-3-fluorophenyl)ethanone (2.8 g) (obtained from 4-bromo-3-fluorobenzonitrile in the same manner as in Step B of Example 30) in tetrahydrofuran (150 mL) was added phenyltrimethylammonium tribromide (4.35 g) at 0C. The reaction mixture was stirred at room temperature for 2 days, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (3.58 g). 1H NMR (300 MHz, CDCl3) δ 4.33-4.42 (2H, m), 7.59-7.77 (3H, m).
2.73 g	With bromine; acetic acid; at 20℃; for 3h;	3-Fluoro-4-bromo-acetophenone (AA_117-1, 2.00 g, 9.22 mmol) was dissolved in acetic acid (15 mL), liquid bromine (0.47 mL, 9.22 mmol) was dripped. The reaction mixture was stirred at room temperature for 3 h. After the reaction was complete as detected by TLC, the solvent was removed by a rotary evaporator to deliver the target compound AA_117-2 (red brown solid, 2.73 g). The product was directly used for the next step without purification. 1H NMR (CDCl3, 400 MHz): δ 7.75-7.66 (m, 3H), 4.39 (s, 2H).

References: [1]Patent: US2016/289212,2016,A1 .Location in patent: Paragraph 0270.
[2]Patent: WO2012/48421,2012,A1 .Location in patent: Page/Page column 24.
[3]Patent: WO2014/19344,2014,A1 .Location in patent: Paragraph 00370.
[4]Patent: US2015/79028,2015,A1 .Location in patent: Paragraph 0837; 0838; 0839.
[5]Patent: EP2848618,2015,A1 .Location in patent: Paragraph 0974.
[6]Patent: US2017/253614,2017,A1 .Location in patent: Paragraph 0614; 0615.

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[ 1003879-02-4 ]
[ 1263483-60-8 ]

References: [1]Patent: US2012/129832,2012,A1 .

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[ 1003879-02-4 ]
[ 1263483-61-9 ]

References: [1]Patent: US2012/129832,2012,A1 .

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[ 1003879-02-4 ]
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[ 1263483-59-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetone; at 20℃; for 2h;	Reference Example 25 2-(4-Bromo-3-fluorophenyl)-2-oxoethyl 2-[4-(5-isopropyl-1,2,4-oxadiazol-3-yl)phenoxy]butanoate Triethylamine (353 μL, 2.53 mmol) was added to an acetone (9.00 mL) solution of the compound obtained in Reference Example 24 (500 mg, 1.69 mmol) and the compound obtained in Reference Example 6 (540 mg, 1.86 mmol) at room temperature, and the mixture was stirred for 2 hours at the same temperature. Water was added to the reaction mixture, and the mixture was subjected to extraction two times with ethyl acetate. The organic layer thus obtained was washed with a saturated sodium hydrogen carbonate solution and saturated brine, and then was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Thus, a crude product of the title compound (854 mg) was obtained.

References: [1]Patent: US2012/129832,2012,A1 .Location in patent: Page/Page column 16.

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Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; acetic acid; In dichloromethane; for 0.166667h;Cooling with ice;	Reference Example 24 2-Bromo-1-(4-bromo-3-fluorophenyl)ethanone A 30% hydrogen bromide-acetic acid solution (3.50 mL, excess amount) was added to a methylene chloride (14.0 mL) solution of the compound obtained in Reference Example 23 (3.35 g, about 13.8 mmol) under ice water cooling, and the mixture was stirred for 10 minutes at the same temperature. Water was added to the reaction mixture, and the mixture was subjected to extraction two times with ethyl acetate. The organic layer thus obtained was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated brine, and then was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was washed with hexane-ethyl acetate (10:1, v/v). Thus, a crude product of the title compound (3.92 g) was obtained.

References: [1]Patent: US2012/129832,2012,A1 .Location in patent: Page/Page column 16.

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[ 695188-21-7 ]
[ 18107-18-1 ]
[ 1003879-02-4 ]
[ 1260857-14-4 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 96(RS)-5-Chloro-N-(2-fluoro-4-(morpholin-2-yl)phenyl)pyrimidin-2-aminea) 2-Bromo-1-(4-bromo-3-fluoro-phenyl)-ethanone & 2-Chloro-1-(4-bromo-3-fluoro-phenyl)-ethanoneTo a stirred solution of 4-bromo-3-fluorobenzoyl chloride (5.4 g, CAS 695188-21-7) in acetonitrile (60 ml) and THF (60m1) at 0-5 C. was added dropwise (trimethylsilyl)diazomethane (13.6 ml, 2 M solution in diethyl ether). The reaction mixture was stirred at room temperature for 30 min. TLC analysis showed the reaction was complete. Hydrobromic acid (5.15 ml) was then added dropwise at 0-5 C. and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was then poured into EtOAc and extracted sequentially with aq. Na2CO3 solution, water and saturated brine. The organic layer was then dried over Na2SO4 and concentrated in vacuo to afford a ca 1:1 mixture of 2-bromo-1-(4-bromo-3-fluoro-phenyl)-ethanone and 2-chloro-1-(4-bromo-3-fluoro-phenyl)-ethanone (6.16 g) as a light yellow solid which was used in the next step without further purification. MS (EI): 203.2 ([{81Br}M1-CH2Cl]+ & [{81Br}M2-CH2Br]+), 201.2 ([{79Br}M1-CH2Cl]+ & [{79Br}M2-CH2Br]+).
		To a stirred solution of 4-bromo-3-fluorobenzoyl chloride (5.4 g, CAS 695188-21-7) in acetonitrile (60 ml) and THF (60ml) at 0-5 C was added dropwise (trimethylsilyl)diazomethane (13.6 ml, 2 M solution in diethyl ether). The reaction mixture was stirred at room temperature for 30 min. TLC analysis showed the reaction was complete. Hydrobromic acid (5.15 ml) was then added dropwise at 0-5 C and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was then poured into EtOAc and extracted sequentially with aq. Na2C03 solution, water and saturated brine. The organic layer was then dried over Na2S04 and concentrated in vacuo to afford a ca 1: 1 mixture of 2-bromo-l-(4-bromo-3-fluoro-phenyl)- ethanone and 2-chloro-l-(4-bromo-3-fluoro-phenyl)-ethanone (6.16 g) as a light yellow solid which was used in the next step without further purification. MS (EI): 203.2 ([{81Br}Mi-CH2Cl]+ & [{ 81Br}M2-CH2Br]+), 201.2 ([{79Br}Mi-CH2Cl]+ & [{79Br}M2-CH2Br]+).

References: [1]Patent: US2012/245172,2012,A1 .Location in patent: Page/Page column 50.
[2]Patent: WO2012/126922,2012,A1 .Location in patent: Page/Page column 88.

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