Azobisisobutyronitrile → 3-(Bromomethyl)-4-chloro-1,1'-biphenyl

HRID 1883630ノート

反応式

HRID 1883630 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[CH3:14].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[CH2:14][Br:15]

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2 回HCID 203296724-Chloro-3-methyl-1,1'-biphenyl

生成物 1

HCID 235081943-(Bromomethyl)-4-chloro-1,1'-biphenyl収率 86.8%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

3.90 g (19.2 mmol) of 4-chloro-3-methylbiphenyl was dissolved in 100 ml of carbon tetrachloride and to this solution was added 632 mg (3.85 mmol) of 2,2′-azobisisobutylonitrile, and the mixture was stirred at room temperature for 15 minutes. To this solution was added 3.43 g (19.2 mmol) of N-bromosuccinimide, and the mixture was stirred for 3.5 hours while heating under reflux. To the reaction solution was further added 632 mg (3.85 mmol) of 2,2′-azobisisobutyronitrile and 300 mg (1.69 mmol) of N-bromosuccinimide, and the mixture was stirred for 2 hours under reflux with heating. The reaction mixture was filtrated, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography (eluant: hexane) to obtain 4.69 g of 2-chloro-5-phenylbenzyl bromide in the form of colorless transparent oil.

後処理

  1. stirringthe mixture was stirred for 3.5 hours
  2. temperaturewhile heating
  3. temperatureunder reflux
  4. stirringthe mixture was stirred for 2 hours
  5. temperatureunder reflux
  6. temperaturewith heating
  7. filtrationThe reaction mixture was filtrated
  8. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-c2045f944fe748f0a0f78d25d3bdf080
出典データセット
uspto-grants-2004_07
特許番号
US06762197B2

反応ノート

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