3-Bromobenzyl bromide → 3-Bromobenzylmethylsulfone

HRID 18422

反応式

HRID 18422 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[CH3:10][S:11]([O-:13])=[O:12].[Na+]>CN(C)C=O>[CH3:10][S:11]([CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Br:1])[CH:3]=1)(=[O:13])=[O:12]

参加物

4

反応物 2

HCID 699793-Bromobenzyl bromideHCID 2733271Sodium methanesulfinate

生成物 1

HCID 27614163-Bromobenzylmethylsulfone収率 67%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 3-bromobenzyl bromide (5.0 g, 20 mmol) in dry dimethylformamide (50 ml) at room temperature under an atmosphere of argon was treated portionwise with sodium methanesulfinate (2.0 g, 20 mmol) with stirring. The mixture was stirred at room temperature for 16 h, and then at 50° C. for 0.5 h. The reaction mix was allowed to cool to room temperature and then partitioned between ethyl acetate and water. The organic layer was separated and dried over sodium sulfate and the solvent removed under reduced pressure to give an oil which was purified by column chromatography on a 50 g isolute silica sep-pak column eluting from 0-100% ethyl acetate in petroleum ether to give the title compound as an off-white solid (3.34 g, 67%).

後処理

  1. stirringThe mixture was stirred at room temperature for 16 h
  2. additionThe reaction mix
  3. custompartitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed under reduced pressure
  7. customto give an oil which
  8. customwas purified by column chromatography on a 50 g isolute silica sep-pak column
  9. washeluting from 0-100% ethyl acetate in petroleum ether

出典と根拠

ORDレコード
ord-46b8d8503a9e4212bad9578f9f61605b
出典データセット
uspto-grants-2010_06
特許番号
US07741351B2

関連ノート

読み込み中…