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

HRID 452644노트

반응식

HRID 452644 반응식
[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

참가 물질

4

반응물 2

HCID 6451240Aluminum(III) ChlorideHCID 60880493HCID 60880493, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e69d070c74b148b28e701d8cd41c52cb
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

반응 노트

불러오는 중…