Aluminum(III) Chloride → 5-Bromo-2,3-dihydro-3,3-dimethylbenzo[b]thiophene

HRID 452644ノート

反応式

HRID 452644 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][C:14]([CH3:17])(O)[CH3:15])=[CH:8][CH:7]=1>C(=S)=S>[Br:5][C:6]1[CH:11]=[CH:10][C:9]2[S:12][CH2:13][C:14]([CH3:17])([CH3:15])[C:8]=2[CH:7]=1

参加物

4

反応物 2

HCID 6451240Aluminum(III) ChlorideHCID 60880493HCID 60880493、化合物

生成物 1

HCID 686640505-Bromo-2,3-dihydro-3,3-dimethylbenzo[b]thiophene収率 34%

試薬・触媒・溶媒 1

HCID 6348Carbon Disulfide溶媒2 回

実験手順

To a suspension of aluminum chloride (10.7 g, 80.0 mmol) in carbon disulfide (80 mL) was added dropwise a solution of 1-[(4-bromophenyl)thio]-2-methylpropan-2-ol (5.22 g, 20.0 mmol) in carbon disulfide (20 mL) at 0° C., and the resulting mixture was stirred at room temperature for 30 min, and heated under reflux for 3 hr. After cooling, the reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane) to give the title compound (1.64 g, yield 34%) as a colorless oil.

後処理

  1. temperatureheated
  2. temperatureunder reflux for 3 hr
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (hexane)

出典と根拠

ORDレコード
ord-e69d070c74b148b28e701d8cd41c52cb
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

反応ノート

読み込み中…