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

Sodium methoxide (2.20 ml of a 4.5M solution in methanol, 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 nitrogen. The reaction was heated under reflux for 3 days and cooled to room temperature. The mixture was concentrated under reduced pressure and the resulting yellow oil was dissolved in dichloromethane (30 ml). The resulting solution was washed with water (2×20 ml) dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel eluting with cyclohexane to provide the title compound (302 mg) as a colourless oil.

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

ORD record

ord-24f56ff5d510486e885e5d07b193e982

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063044B2