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

HRID 1709662노트

반응식

HRID 1709662 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-a87c250ef91449c1ba95a28514ddbcab
출처 데이터셋
uspto-grants-1990_08
특허 번호
US04950673

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