4-Methoxyphenol → 2-Bromo-4-methoxyphenol

A solution of 2.6 mL (100 mmol) bromine in 10 mL carbon disulfide was added dropwise over 30 minutes to a solution of 12.4 gm (100 mMol) 4-methoxyphenol in 20 mL carbon disulfide at 0° C. After 30 minutes an additional 1 mL of bromine in 10 mL carbon disulfide are added dropwise. The reaction mixture was then concentrated under reduced pressure and the residue was dissolved in diethyl ether. This solution was washed sequentially with 100 mL water and 100 mL saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with a gradient of hexane containing from 0 to 20% ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 11.6 gm (57%) of the desired compound as a crystalline solid.

1. concentrationThe reaction mixture was then concentrated under reduced pressure
2. dissolutionthe residue was dissolved in diethyl ether
3. washThis solution was washed sequentially with 100 mL water and 100 mL saturated aqueous sodium chloride
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. washeluting with a gradient of hexane containing from 0 to 20% ethyl acetate
7. additionFractions containing product
8. concentrationconcentrated under reduced pressure

ORD record

ord-0c20bd811439434c83127a3260b9b438

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06967201B1