Bromoform → (2,2-Dibromocyclopropyl)benzene

HRID 1470056노트

반응식

HRID 1470056 반응식
[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

참가 물질

6

반응물 3

HCID 5558BromoformHCID 7501StyreneHCID 14797Potassium Hydroxide

생성물 1

HCID 220379(2,2-Dibromocyclopropyl)benzene수율 88%

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-16ba12f2c9a3412d9463d97f4b81c0a4
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006403B2

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