Reaction #2348126

Reaction equation

NaOH

water

1-Methanesulfonyl-3-methoxy benzene

bromine

→

1-bromo-2-methanesulfonyl-4-methoxy benzene

Yield 45.0%

Solvents

acetic acid

acetic acid

Conditions

Workup

1. 1
   Extractionextracted with EtOAc (3×200 mL)
2. 2
   Dryingdried over Na2SO4
3. 3
   OtherThe crude compound was purified by column chromatography (SilicaGel 230-400 mesh

Procedure

1-Methanesulfonyl-3-methoxy benzene was dissolved in 90 mL glacial acetic acid. 100 mL water was added. A solution of bromine (4.79 g, 30 mmol) in 10 mL acetic acid was added dropwise at 10° C. The stirring was continued at rt for 15 h. The pH of the mixture was adjusted to pH 8 with aqueous NaOH solution, and extracted with EtOAc (3×200 mL) and dried over Na2SO4. The crude compound was purified by column chromatography (SilicaGel 230-400 mesh; 20% EtOAc in hexanes as an eluent) to give 1-bromo-2-methanesulfonyl-4-methoxy benzene (2.4 g, 45%).

Source