Water → 4-Bromo-1-fluoro-2-(methoxymethyl)benzene

To a solution of (5-bromo-2-fluorophenyl)methanol (5.00 g) in THF (100 ml) was added 60% sodium hydride (1.08 g) at 0° C., and the mixture was stirred at room temperature for 30 min. Methyl iodide (3.80 ml) was added, and the mixture was stirred for 1.5 h. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by column chomatography (eluent, hexane→hexane:ethyl acetate=50:1) to give the title compound (4.86 g) as a brown oil.

1. stirringthe mixture was stirred for 1.5 h
2. extractionthe mixture was extracted with ethyl acetate
3. washwashed with saturated brine
4. customdried
5. customThe solvent was evaporated under reduced pressure
6. customthe residue was purified by column chomatography (eluent, hexane→hexane:ethyl acetate=50:1)

ORD record

ord-2d70ab7af45e46089630058db1ad1a66

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06518257B1