Carbon Tetrachloride → 1-(Bromomethyl)-2-chloro-3-methyl-5-nitrobenzene

HRID 374542

反応式

HRID 374542 の反応式
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.ClC(Cl)(Cl)Cl>O>[Br:13][CH2:8][C:7]1[CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=[C:3]([CH3:12])[C:2]=1[Cl:1]

参加物

6

反応物 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl Peroxide2 回HCID 67184N-bromobutanimideHCID 99205692-Chloro-1,3-dimethyl-5-nitrobenzene

生成物 1

HCID 189972501-(Bromomethyl)-2-chloro-3-methyl-5-nitrobenzene収率 70.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 129 g of 2-chloro-1,3-dimethyl-5-nitrobenzene, 125 g of 1-bromo-2,5-pyrrolidinedione, 12 g of dibenzoyl peroxide and 1200 ml of tetrachloromethane was stirred for 2 hours at reflux temperature using a water separator. Twice there was added an extra portion of 20 g of dibenzoyl peroxide during a refluxing period of 29 hours. After cooling, the reaction mixture was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /hexane 50:50). The eluent of the desired fraction was evaporated, yielding 130 g (70.2%) of 1-(bromomethyl)-2-chloro-3-methyl-5-nitrobenzene (interm. 5).

後処理

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /hexane 50:50)
  8. customThe eluent of the desired fraction was evaporated

出典と根拠

ORDレコード
ord-a2d6793df1834518a51fc3a7edf07cbf
出典データセット
uspto-grants-1996_01
特許番号
US05480912

関連ノート

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