1-(4-bromophenyl)sulfanyl-2-methylpropan-2-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. heated under reflux for 3 hr After cooling 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 concentrated under reduced pressure The residue was purified by basic silica gel column chromatography (hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromothiophenol (9.45 g, 50.0 mmol) in tetrahydrofuran (150 mL) was added sodium hydride (60% in oil, 2.20 g, 55.0 mmol) at 0° C. by small portions, and the resulting mixture was stirred for 1 hr. To this reaction mixture was added isobutylene oxide (4.91 mL, 55.0 mmol), and the resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (11.6 g, yield 89%) as a colorless oil. the resulting mixture was stirred overnight at room temperature washed with water and saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromothiophenol (9.45 g, 50.0 mmol) in tetrahydrofuran (150 mL) was added sodium hydride (60% in oil, 2.20 g, 55.0 mmol) at 0° C. by small portions, and the resulting mixture was stirred for 1 hr. To this reaction mixture was added isobutylene oxide (4.91 mL, 55.0 mmol), and the resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (11.6 g, yield 89%) as a colorless oil. the resulting mixture was stirred overnight at room temperature washed with water and saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. heated under reflux for 3 hr After cooling 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 concentrated under reduced pressure The residue was purified by basic silica gel column chromatography (hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromothiophenol (9.45 g, 50.0 mmol) in tetrahydrofuran (150 mL) was added sodium hydride (60% in oil, 2.20 g, 55.0 mmol) at 0° C. by small portions, and the resulting mixture was stirred for 1 hr. To this reaction mixture was added isobutylene oxide (4.91 mL, 55.0 mmol), and the resulting mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (11.6 g, yield 89%) as a colorless oil. the resulting mixture was stirred overnight at room temperature washed with water and saturated brine dried over anhydrous magnesium sulfate concentrated under reduced pressure The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=1/1)