1-Bromo-3-chloro-5-fluorobenzene → 1-Bromo-3-chloro-5-methoxybenzene

Sodium methoxide (4.5M solution in methanol, 2.20 ml, 10.0 mmol) was added dropwise to a stirred solution of 1-fluoro-3-chloro-5-bromobenzene (1.00 g, 4.77 mmol) in methanol (28 ml) at room temperature under a nitrogen atmosphere. The mixture was heated under reflux for 3 days and then cooled to room temperature. The mixture was evaporated under reduced pressure and the resulting yellow oil was dissolved in dichloromethane (30 ml). The dichloromethane solution was washed with water (2×20 ml) dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel eluting with cyclohexane to provide the title compound as a colourless oil (302 mg).

1. temperatureThe mixture was heated
2. temperatureunder reflux for 3 days
3. customThe mixture was evaporated under reduced pressure
4. dissolutionthe resulting yellow oil was dissolved in dichloromethane (30 ml)
5. washThe dichloromethane solution was washed with water (2×20 ml)
6. dry with materialdried over magnesium sulphate
7. filtrationfiltered
8. customevaporated under reduced pressure
9. customThe residue was purified by chromatography on silica gel eluting with cyclohexane

ORD record

ord-9ea07e737a7c4e359e4a44e61f2d3707

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06933312B2