Potassium Carbonate → 2-Bromo-1-(2,4-difluorophenoxy)-4-(trifluoromethyl)benzene

HRID 2170207

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1F.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[OH:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[O:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[F:13]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-bromo-4-fluorobenzotrifluoride (0.5 mL, 3.52 mmol), 2,4-difluorophenol (0.337 mL, 3.52 mmol), and potassium carbonate (0.486 g, 3.52 mmol) in dimethylformamide (7 mL) was heated at 80° C. overnight. The reaction mixture was cooled to ambient temperature and partitioned between ethyl acetate and water. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation. The crude material was purified by flash chromatography (ethyl acetate/hexanes) to provide the title compound (1.0 g, 80% yield).

Workup

temperatureThe reaction mixture was cooled to ambient temperature
custompartitioned between ethyl acetate and water
customThe layers were separated
extractionthe aqueous layer was extracted with ethyl acetate
washThe combined organics were washed with water and saturated aqueous sodium chloride
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated by rotary evaporation
customThe crude material was purified by flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-8058b1143cce49648c28259edfb111e8
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050346B2

Linked notes

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