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

Under 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. The mixture was stirred under reflux for 13 hours. Insoluble substances were filtered off and the solvent was distilled off under reduced pressure. By adding ethyl acetate (150 mL) and water (100 mL) to the residue, the reaction mixture was allowed to separate into layers. An organic layer was washed successively with water (100 mL), a 5% NaHCO3 aqueous solution (100 mL) and a 5% NaCl aqueous solution (100 mL), dried over anhydrous magnesium sulfate and then naturally filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (56.1 g, brown oil). Yield 95.2%.

1. temperatureunder reflux for 13 hours
2. filtrationInsoluble substances were filtered off
3. distillationthe solvent was distilled off under reduced pressure
4. additionBy adding ethyl acetate (150 mL) and water (100 mL) to the residue
5. customto separate into layers
6. washAn organic layer was washed successively with water (100 mL)
7. dry with materiala 5% NaHCO3 aqueous solution (100 mL) and a 5% NaCl aqueous solution (100 mL), dried over anhydrous magnesium sulfate
8. filtrationnaturally filtered
9. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-5222fa7c72514e5cb2a1eed80633f81a

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07135582B2