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

HRID 1709662ノート

反応式

HRID 1709662 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 140330355-(Bromomethyl)-2-chlorobenzonitrile収率 30.4%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 241Benzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a87c250ef91449c1ba95a28514ddbcab
出典データセット
uspto-grants-1990_08
特許番号
US04950673

反応ノート

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