Hydrogen Bromide → 1-(2-Bromopyridin-4-yl)-2-(4-fluorophenyl)ethanone

HRID 986970

반응식

HRID 986970 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8](=[O:19])[CH:9](C#N)[C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.[BrH:20]>C(=O)(O)[O-].[Na+]>[Br:20][C:2]1[CH:7]=[C:6]([C:8](=[O:19])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1

참가 물질

4

반응물 2

HCID 260Hydrogen BromideHCID 229879671-(2-Chloropyridin-4-yl)-2-cyano-2-(4-fluorophenyl)ethanone

생성물 1

HCID 229880011-(2-Bromopyridin-4-yl)-2-(4-fluorophenyl)ethanone

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매2회

반응 조건

온도
135 °C

실험 절차

To 1-(2-chloropyridin-4-yl)-2-cyano-2-(4-fluorophenyl)ethanone (22.0 g, 80 mmol) was added 48% hydrobromic acid (75 ml) and the reaction mixture was heated at reflux in an oil bath at 135° C. After 4 h, the reaction mixture was allowed to cool to room temperature and then further cooled in an ice bath. Saturated sodium bicarbonate (100 ml) was carefully added, followed by solid portions of sodium bicarbonate until the pH of the reaction mixture was neutral. The reaction mixture was then extracted with ethyl acetate and the ethyl acetate layer was dried over sodium sulfate, filtered and concentrated to a brown semi-solid (2.8 g). The crude product was purified by flash chromatography on silica gel, eluting with 1:1 mixture of ethyl acetate/hexanes to give 1-(2-bromopyridin-4-yl)-2-(4-fluorophenyl)ethanone (1.9 g).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureto cool to room temperature
  3. temperaturefurther cooled in an ice bath
  4. extractionThe reaction mixture was then extracted with ethyl acetate
  5. dry with materialthe ethyl acetate layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a brown semi-solid (2.8 g)
  8. customThe crude product was purified by flash chromatography on silica gel
  9. washeluting with 1:1 mixture of ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-131f3886240d43afa5dd9392df4d5a89
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06630485B2

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