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 at 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. temperatureat 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-3288d1c71aeb41fba8ec97562fb2c5f9

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157468B2