Azobisisobutyronitrile → 2-(Bromomethyl)-6-chlorobenzonitrile

HRID 1752245노트

반응식

HRID 1752245 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.ClCCl>[Br:11][CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[C:3]=1[C:4]#[N:5]

참가 물질

6

반응물 3

HCID 6547AzobisisobutyronitrileHCID 230532-Chloro-6-methylbenzonitrileHCID 67184N-bromobutanimide

생성물 1

HCID 667339472-(Bromomethyl)-6-chlorobenzonitrile수율 46.7%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-chloro-6-methylbenzonitrile (2.0 g, 13 mmol) and N-bromosuccinimide (2.6 g, 15 mmol) in carbon tetrachloride (20 mL) was added azobisisobutyronitrile (0.20 g, 1.2 mmol). The mixture was refluxed for 3 h and then cooled, diluted with dichloromethane and washed with water and brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resultant oil was purified via flash column chromatography (ethyl acetate:hexane, 0:100 to 30:70) to yield white solid product (1.4 g, 46%). 1H NMR (400 MHz, CDCl3) δ 7.43-7.59 (m, 3H), 4.64 (s, 2H).

후처리

  1. temperatureThe mixture was refluxed for 3 h
  2. temperaturecooled
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant oil was purified via flash column chromatography (ethyl acetate:hexane, 0:100 to 30:70)

출처 및 근거

ORD 기록
ord-15bbc06972cc442d96d857f173004298
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163003B2

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