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

HRID 1017663

反応式

HRID 1017663 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒2 回

反応条件

温度
135 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-79eacb8b118a4364bfdc16d53c65f9d5
出典データセット
uspto-grants-2002_11
特許番号
US06479507B2

関連ノート

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