Benzoyl Peroxide → 1-(Bromomethyl)-2-chloro-3-nitrobenzene

HRID 629986

反応式

HRID 629986 の反応式
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:11].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[Cl:1]

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 775912-Chloro-3-nitrotoluene

生成物 1

HCID 183630451-(Bromomethyl)-2-chloro-3-nitrobenzene収率 47.2%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

2-chloro-1-methyl-3-nitrobenzene (1 g, 5.8 mmol) was dissolved in CCl4 (10 mL), then N-bromosuccinimide (2.28 g, 12.8 mmol) and benzoyl peroxide (846 mg, 3.5 mmol) were added. The mixture was stirred overnight at reflux. The solid was removed by filtration, and the filtrate was washed with water and dried over sodium sulfate. After evaporation of the solvent, the residue was dissolved in DCM and purified on silica gel using 30% hexane/AcOEt to afford 1-(bromomethyl)-2-chloro-3-nitrobenzene (686 mg, 47% yield); 1H NMR (400 MHz, CDCl3): δ 4.64 (s, 2H), 7.42 (t, J=7.9 Hz, 1H), 7.67 (dd, J=1.6 Hz, J=7.9 Hz, 1H), 7.75 (dd, J=1.6 Hz, J=7.9 Hz, 1H).

後処理

  1. temperatureat reflux
  2. customThe solid was removed by filtration
  3. washthe filtrate was washed with water
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent
  6. dissolutionthe residue was dissolved in DCM
  7. custompurified on silica gel using 30% hexane/AcOEt

出典と根拠

ORDレコード
ord-11beda3f34914e3da2669082653370b9
出典データセット
uspto-grants-2016_04
特許番号
US09315521B2

関連ノート

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