Water → 1-Bromo-3-(1-methoxyethyl)benzene

HRID 334063ノート

反応式

HRID 334063 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:10]([OH:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1.[CH3:13]I.O>CN(C=O)C>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([O:12][CH3:13])[CH3:11])[CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 984791-(3-Bromophenyl)ethanol

生成物 1

HCID 685942561-Bromo-3-(1-methoxyethyl)benzene

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a stirred and ice-cooled mixture of 1.09 g (27.4 mmol) NaH (60% in mineral oil) in 20 mL dry DMF was added a solution of 5.00 g (24.9 mmol) 1-(3-bromo-phenyl)-ethanol in 10 mL dry DMF under argon atmosphere. The mixture was stirred for 30 min at 0° C. 1.70 mL (27.4 mmol) methyl iodide was added and stirring was continued for 4 h at RT. The mixture was worked up by adding water, followed by extraction with EtOAc. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (Cyc/EtOAc=9/1).

後処理

  1. temperatureice-cooled
  2. stirringThe mixture was stirred for 30 min at 0° C
  3. stirringstirring
  4. extractionfollowed by extraction with EtOAc
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography (Cyc/EtOAc=9/1)

出典と根拠

ORDレコード
ord-dc681b71c0d240e186108f56f463d81c
出典データセット
uspto-grants-2014_11
特許番号
US08883789B2

反応ノート

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