Potassium Carbonate → HCID 24695760, compound

To a solution of 2-bromo-4-fluorophenol (1.2 g, 6.28 mmol) in acetonitrile (10 ml) was added potassium carbonate (2.78 g, 20 mmol) and 2-bromoethyl methyl ether (0.85 ml, 9.5 mmol). The resultant solution was heated to reflux for 16 hours. The reaction mixture was cooled then concentrated in vacuo. tert-Butyl-dimethyl ether (20 ml) and sodium hydroxide (1M aqueous solution) (10 ml) were added and the layers were separated. The organic layer was washed with saturated brine solution (10 ml) then dried over anhydrous Na2SO4 (s), filtered and evaporated in vacuo. Purification by column chromatography on silica gel eluting with heptane to heptane:ethyl acetate (9:1) afforded the title compound as a colourless oil (1.03 g, 66%).

1. temperatureto reflux for 16 hours
2. temperatureThe reaction mixture was cooled
3. concentrationthen concentrated in vacuo
4. additiontert-Butyl-dimethyl ether (20 ml) and sodium hydroxide (1M aqueous solution) (10 ml) were added
5. customthe layers were separated
6. washThe organic layer was washed with saturated brine solution (10 ml)
7. dry with materialthen dried over anhydrous Na2SO4 (s)
8. filtrationfiltered
9. customevaporated in vacuo
10. customPurification by column chromatography on silica gel eluting with heptane to heptane:ethyl acetate (9:1)

ORD record

ord-a699c5020da04c888be6b4d8c784f779

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08134007B2