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

HRID 2414142ノート

反応式

HRID 2414142 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-9b8704a1b48d4b38a3f7d6ac01b980f9
出典データセット
uspto-grants-1988_01
特許番号
US04721791

反応ノート

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