Carbon tetrabromide → 2,4-Dichloro-1-(2,2-dibromovinyl)benzene

HRID 275688ノート

反応式

HRID 275688 の反応式
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11](Br)(Br)([Br:13])[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:12][C:11]([Br:13])=[CH:4][C:3]1[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=1[Cl:1]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 134042,4-Dichlorobenzaldehyde

生成物 1

HCID 120184412,4-Dichloro-1-(2,2-dibromovinyl)benzene収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Into a solution of 2,4-dichlorobenzaldehyde (8.7 g, 50 mmol) and carbon tetrabromide (18.3 g, 55 mmol) in dichloromethane (200 ml) was added portionwise triphenylphosphine (28.8 g, 10 mmol) at 0° C. The slightly yellow mixture was stirred at room temperature for 1 hour and diluted with hexanes (800 ml). This mixture was then filtrated through a short silica gel column with 1:10 ethyl acetate-hexanes and the filtrate was concentrated in vacuo to give a white solid (16.5 g, 100%). recrystallization from ether-hexanes gave a white crystalline product (14.2 g, 86% yield); 1H NMR (TMS/CDCl3):

後処理

  1. filtrationThis mixture was then filtrated through a short silica gel column with 1:10 ethyl acetate-hexanes
  2. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-ca95d610605f49c784332b1e39b8b2d1
出典データセット
uspto-grants-2002_03
特許番号
US06352990B1

反応ノート

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