Sulfuric Acid → 5-Bromo-2-tert-butylphenol

To a solution of 29.46 g (170.3 mmol) of 3-bromophenol (distilled) and 16.41 g (20.9 ml, 221.3 mmol) of t-butanol in 100 ml of carbon tetrachloride was added 20.0 ml of conc. sulfuric acid. The clear, colorless solution turned a dark magenta color and became hot. The solution was cooled in water (ambient temperature) and allowed to stir at room temperature for 84 hours. The reaction mixture was neutralized with sat. aqueous NaHCO3 solution (pH~7.0), partitioned between 300 ml of water and 500 ml of dichloromethane, and the organic and aqueous layers were separated. The aqueous phase was washed with 2×500 ml-portions of dichloromethane. All organic phases were combined, washed with 400 ml of brine solution, dried over MgSO4, filtered and concentrated in vacuo to a purple oil. Purification by flash chromatography (silica, 5% ethyl acetate in hexane) followed by kugelrohr distillation yielded the title compound as a clear, slightly yellow oil.

1. custompartitioned between 300 ml of water and 500 ml of dichloromethane
2. customthe organic and aqueous layers were separated
3. washThe aqueous phase was washed with 2×500 ml-portions of dichloromethane
4. washwashed with 400 ml of brine solution
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo to a purple oil
8. customPurification by flash chromatography (silica, 5% ethyl acetate in hexane)
9. distillationfollowed by kugelrohr distillation

ORD record

ord-2f786232655d4388b8cfc0b4d474741c

Source dataset

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05498795