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

HRID 2170207노트

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HRID 2170207 반응식
[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]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 1230512,4-DifluorophenolHCID 1442953-Bromo-4-fluorobenzotrifluoride

생성물 1

HCID 896562892-Bromo-1-(2,4-difluorophenoxy)-4-(trifluoromethyl)benzene수율 80.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-8058b1143cce49648c28259edfb111e8
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09050346B2

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