Bromoform → (2,2-Dibromocyclopropyl)benzene

HRID 1470056ノート

反応式

HRID 1470056 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-16ba12f2c9a3412d9463d97f4b81c0a4
出典データセット
uspto-grants-2015_04
特許番号
US09006403B2

反応ノート

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