Dimethyl Sulfate → 2-Bromo-4-chloroanisole

A rapidly stirred solution of 15.5 grams (0.074 mole) of 2-bromo-4-chlorophenol, 20.0 grams (0.145 mole) of anhydrous powdered potassium carbonate, and 10 mL (0.106 mole) of dimethyl sulfate in 150 mL of acetone was heated at reflux for about 18 hours. After this time, the reaction mixture was concentrated under reduced pressure to a residue. The residue was partitioned between 100 mL each of water and methylene chloride. The organic layer was removed and washed with an aqueous solution saturated with sodium chloride. The organic layer was then dried with magnesium sulfate and filtered. The filtrate was passed through a short column of silica gel. Elution was accomplished with 500 mL of methylene chloride. The eluate was concentrated under reduced pressure, yielding 16.3 grams of 3-bromo-4-methoxychlorobenzene. The NMR spectrum was consistent with the proposed structure.

1. temperatureat reflux for about 18 hours
2. concentrationAfter this time, the reaction mixture was concentrated under reduced pressure to a residue
3. customThe residue was partitioned between 100 mL each of water and methylene chloride
4. customThe organic layer was removed
5. washwashed with an aqueous solution saturated with sodium chloride
6. dry with materialThe organic layer was then dried with magnesium sulfate
7. filtrationfiltered
8. washElution
9. concentrationThe eluate was concentrated under reduced pressure

ORD record

ord-a8f805b638364897878624b960472a82

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05534518