Azobisisobutyronitrile → 4-(Bromomethyl)-1-chloro-2-methoxybenzene

HRID 17905

反応式

HRID 17905 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10].C1C(=O)N([Br:18])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:9][CH3:10])[CH:4]=1

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 993521-Chloro-2-methoxy-4-methylbenzene

生成物 1

HCID 136628594-(Bromomethyl)-1-chloro-2-methoxybenzene収率 92%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

To a solution of 1-chloro-2-methoxy-4-methyl-benzene (50 g, 0.32 mol) in CCl4 (350 mL) was added NBS (57.2 g, 0.32 mol) and AIBN (10 g, 60 mmol). The mixture was heated at reflux for 3 hours. The solvent was evaporated under vacuum and the residue was purified by column chromatography on silica gel (Petroleum Ether/EtOAc=20:1) to give 4-bromomethyl-1-chloro-2-methoxy-benzene (69 g, 92%). 1H NMR (400 MHz, CDCl3) δ 7.33-7.31 (m, 1H), 6.95-6.91 (m, 2H), 4.46 (s, 2H), 3.92 (s, 3H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. customThe solvent was evaporated under vacuum
  4. customthe residue was purified by column chromatography on silica gel (Petroleum Ether/EtOAc=20:1)

出典と根拠

ORDレコード
ord-127a3157d14c402ba00add575389526d
出典データセット
uspto-grants-2010_06
特許番号
US07741321B2

関連ノート

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