Dimethyl Sulfate → 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene

Under an argon atmosphere, to a solution of 4-bromo-2,6-di-tert-butylphenol (50 g, 0.175 moL) and potassium carbonate (96.7 g, 4.0 equivalents) in acetone (750 mL) was added dimethyl sulfate (38.6 g, 1.75 equivalents) at 22° C., and the mixture was stirred under reflux for 13 hrs. Insoluble materials were filtered off and the solvent was evaporated under reduced pressure. Ethyl acetate (150 mL) and water (100 mL) were added, the mixture was partitioned, and the organic layer was washed successively with water (100 mL), 5% aqueous NaHCO3 solution (100 mL) and 5% aqueous NaCl solution (100 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and the filtrate was concentrated under reduced pressure to give the title compound (56.1 g, brown oil). yield 95.2%

1. temperatureunder reflux for 13 hrs
2. filtrationInsoluble materials were filtered off
3. customthe solvent was evaporated under reduced pressure
4. additionEthyl acetate (150 mL) and water (100 mL) were added
5. customthe mixture was partitioned
6. washthe organic layer was washed successively with water (100 mL), 5% aqueous NaHCO3 solution (100 mL) and 5% aqueous NaCl solution (100 mL)
7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
8. filtrationfiltered by gravity
9. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-bfe0f31f65a1405bbf9a90beb0c8e593

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07208633B2