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

HRID 986970

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

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

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

出典と根拠

ORDレコード: ord-131f3886240d43afa5dd9392df4d5a89
出典データセット: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06630485B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

関連ノート