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

To a solution of 1-bromo-3-chloro-5-fluorobenzene (25 g, 120 mmol) in methanol (800 ml) was added sodium methoxide (64 g, 1180 mmol). The reaction was heated to reflux for 9 days. The reaction was then concentrated in vacuo to one fifth of the volume (150 ml), cooled. and water (1000 ml) added. The mixture was extracted with diethyl ether (3×150 ml). The combined organic extracts were washed with brine (2×100 ml), dried over Na2SO4 and evaporated to afford the title compound (24.6 g).

1. temperatureThe reaction was heated
2. temperatureto reflux for 9 days
3. concentrationThe reaction was then concentrated in vacuo to one fifth of the volume (150 ml)
4. temperaturecooled
5. additionand water (1000 ml) added
6. extractionThe mixture was extracted with diethyl ether (3×150 ml)
7. washThe combined organic extracts were washed with brine (2×100 ml)
8. dry with materialdried over Na2SO4
9. customevaporated

ORD record

ord-41e19a2005d34698aed4fe0ae35226b2

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08134007B2