N-bromobutanimide → 5-(Bromomethyl)-2-chlorobenzonitrile

HRID 1194716노트

반응식

HRID 1194716 반응식
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[C:4]#[N:5].[Br:11]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][Br:11])=[CH:6][C:3]=1[C:4]#[N:5]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 125572002-Chloro-5-methylbenzonitrile

생성물 1

HCID 140330355-(Bromomethyl)-2-chlorobenzonitrile수율 30.4%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 241Benzene용매

실험 절차

A mixture of 2-chloro-5-methylbenzonitrile (10.6 g, 69.9 mmol), N-bromosuccinimide (12.2 g, 68.5 mmol), and dibenzoyl peroxide (349 mg, 1.44 mmol) in benzene (350 ml) was refluxed 1.5 hours, cooled, and evaporated to dryness under vacuum. The residue was suspended in 7:3 (v/v) hexane-dichloromethane, filtered, and evaporated. The crude product was chromatographed on silica gel (650 g) eluted with 7:3 (v/v) hexane-dichloromethane to provide 4.8 g (30%) 4-chloro-3-cyanobenzyl bromide, m.p. 55°-58° C.

후처리

  1. temperaturewas refluxed 1.5 hours
  2. temperaturecooled
  3. customevaporated to dryness under vacuum
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was chromatographed on silica gel (650 g)
  7. washeluted with 7:3 (v/v) hexane-dichloromethane

출처 및 근거

ORD 기록
ord-df76d66bf66e4a0f825f92a8343fa05c
출처 데이터셋
uspto-grants-1989_03
특허 번호
US04816469

반응 노트

불러오는 중…