Water → 1-(4-Fluorophenyl)-2-hydroxyethanone

Under a nitrogen atmosphere, a stirred solution of 4′-fluoroacetophenone (1.15 g, 8.32 mmol) in acetonitrile (42 ml) was treated with [bis(trifluoroacetoxy)iodo]benzene (7.16 g, 16.6 mmol) followed by water (8.3 ml) and trifluoroacetic acid (1.3 ml). The resultant solution was heated under reflux for 2 hr before standing overnight at ambient temperature. The solvent was then removed in vacuo; water (30 ml) was added and the mixture extracted with dichloromethane (3×30 ml). The combined extracts were washed with saturated sodium hydrogen carbonate solution (30 ml) followed by brine (30 ml) and dried (MgSO4). The solvent was removed in vacuo to give the crude 1-(4-fluorophenyl)-2-hydroxyethanone which was purified by flash chromatography (silica) eluting with ethyl acetate and 40°-60° C. petroleum ether (3:1) to give a white solid (0.55 g).

1. temperatureunder reflux for 2 hr
2. customThe solvent was then removed in vacuo
3. additionwater (30 ml) was added
4. extractionthe mixture extracted with dichloromethane (3×30 ml)
5. washThe combined extracts were washed with saturated sodium hydrogen carbonate solution (30 ml)
6. dry with materialdried (MgSO4)
7. customThe solvent was removed in vacuo
8. customto give the crude 1-(4-fluorophenyl)-2-hydroxyethanone which
9. customwas purified by flash chromatography (silica)
10. washeluting with ethyl acetate and 40°-60° C. petroleum ether (3:1)

ORD record

ord-e19cf1caa0714f40ad8c54c3c0d4e86f

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456187B2