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

HRID 452644Notes

Reaction equation

HRID 452644 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-e69d070c74b148b28e701d8cd41c52cb
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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