1,3,5-Tribromobenzene → 3,5-Dibromoanisole

Temperature

90 °C

Sodium methoxide (25 g; WAKO) was added to a DMF (250 mL) solution of 1,3,5-tribromobenzene (75 g; TCI) and the resulting mixture was stirred at 90° C. for 15 minutes. The reaction mixture was concentrated, aqueous ammonium chloride (400 mL) and ethyl acetate (400 mL) were added to extract the reaction mixture, the organic layer was washed with saturated brine (200 mL×2), and the organic layer was dried. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (n-hexane) to give the title compound (39.2 g).

1. concentrationThe reaction mixture was concentrated
2. additionaqueous ammonium chloride (400 mL) and ethyl acetate (400 mL) were added
3. extractionto extract the reaction mixture
4. washthe organic layer was washed with saturated brine (200 mL×2)
5. customthe organic layer was dried
6. customThe solvent was evaporated under reduced pressure
7. customthe residue was purified by column chromatography (n-hexane)

ORD record

ord-aec4e1909a5c4f9299872de1c70009ca

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299055B2