Bromoform → (2,2-Dibromocyclopropyl)benzene

HRID 2061796ノート

反応式

HRID 2061796 の反応式
[CH:1]([Br:4])(Br)[Br:2].[CH2:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[Br:2][C:1]1([Br:4])[CH2:5][CH:6]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

6

反応物 3

HCID 5558BromoformHCID 7501StyreneHCID 14797Potassium Hydroxide

生成物 1

HCID 220379(2,2-Dibromocyclopropyl)benzene収率 88%

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

In a 1 liter 3-neck flask, bromoform (312 g, 1.23 mol) was added dropwise over 120 min to stirred solution of styrene (100 g, 0.96 mol), benzyltriethylammonium chloride (7 g, 0.031 mol) and powdered potassium hydroxide (80.6 g, 1.44 mol) in dichloromethane (480 mL) at 40° C. The mixture was stirred at 25° C. for 20 h. The reaction mixture was filtered through a short plug of silica and the filtrate was concentrated. The dark residue was distilled at 80° C. under reduced pressure (about 50 Pa) to give the desired product as pale yellow liquid (233 g, yield 88%, purity 98% by HPLC(UV)). 1H NMR (CDCl3, 400 MHz): δ 7.38˜7.42 (m, 3H), 7.29˜7.31 (m, 2H), 2.98˜3.03 (m, 1H), 2.15˜2.20 (m, 1H), 2.04˜2.08 (m, 1H).

後処理

  1. filtrationThe reaction mixture was filtered through a short plug of silica
  2. concentrationthe filtrate was concentrated
  3. distillationThe dark residue was distilled at 80° C. under reduced pressure (about 50 Pa)

出典と根拠

ORDレコード
ord-68733d94166f485990519797662af204
出典データセット
uspto-grants-2012_10
特許番号
US08283454B2

反応ノート

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