Hydrogen Bromide → 1,1,1-Trifluoro-4-(4-hydroxyphenyl)butan-2-one

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Reaction Conditions

Reaction Steps

A 100 mL round bottom flask, fitted with reflux condenser, magnetic stirrer and argon inlet was charged with 2.05 g (6.7 mM) of ethyl 3-(4-methoxyphenyl)-2-(1-oxo-2,2,2-trifluoroethyl)propionate, 20 mL of 31% HBr in AcOH, and 10 mL of water. This mixture was heated overnight at 120° C., concentrated under reduced pressure and partitioned between dichloromethane and water. The organic layer was extracted with aqueous bisulfite, saturated sodium bicarbonate, dried (anhydrous MgSO4), and the solvent removed under reduced pressure. The crude reaction mixture was chromatographed on a 50×300 mm silica gel column with 1:1 ethyl acetate:hexane. Similar fractions were combined and solvent was removed under reduced pressure to yield 600 mg (41%) as a clear oil. nmr(CDCl3)--α2.95(m, 4H), 4.90(bs, 1H), 6.93(dd, 4H) J=4, 60 Hz.

Provenance & Evidence