N-bromobutanimide → 2-Bromomethyl-5-chloro-4-nitrobenzonitrile

HRID 1739835ノート

反応式

HRID 1739835 の反応式
[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[C:7]#[N:8].C1C(=O)N([Br:21])C(=O)C1>ClC1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:21][CH2:10][C:5]1[CH:4]=[C:3]([N+:11]([O-:13])=[O:12])[C:2]([Cl:1])=[CH:9][C:6]=1[C:7]#[N:8]

参加物

5

反応物 2

HCID 67184N-bromobutanimide2 回HCID 102417995-Chloro-2-methyl-4-nitrobenzonitrile

生成物 1

HCID 154289152-Bromomethyl-5-chloro-4-nitrobenzonitrile収率 108.9%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒2 回HCID 7964Chlorobenzene溶媒

反応条件

温度
130 °C

実験手順

A mixture of 5-chloro-4-nitro-2-methylbenzonitrile (32.0 g, 0.16 mol), NBS (54.0 g, 0.30 mol) and benzoyl peroxide (200 mg, catalytic amount) in chlorobenzene was heated at 130° C. and irradiated with a sunlamp for 15 h. More NBS (30.0 g, 0.17 mol) and benzoyl peroxide (200 mg) were added. The mixture was further reacted for 24 h. After cooling, the precipitate formed was filtered off and washed with CH2Cl2. The combined filtrates were washed with H2O (2×), dried over anhydrous MgSO4 and concentrated in vacuo. The residue was then chromatographed over silica gel and eluted with hexanes:EtOAc (9:1) to give 2-bromomethyl-5-chloro-4-nitrobenzonitrile (48 g, contaminated with starting material and dibrominated product) as a pale yellow solid.

後処理

  1. customirradiated with a sunlamp for 15 h
  2. customThe mixture was further reacted for 24 h
  3. temperatureAfter cooling
  4. customthe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with CH2Cl2
  7. washThe combined filtrates were washed with H2O (2×)
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was then chromatographed over silica gel
  11. washeluted with hexanes:EtOAc (9:1)

出典と根拠

ORDレコード
ord-154b6c551aee4eeaa57aabc2ee6bcb65
出典データセット
uspto-grants-1999_10
特許番号
US05968958

反応ノート

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