Trifluoroacetic acid → HCID 67071657, compound

Participants

Reaction Steps

To a solution of 3-(3-ethoxy-phenyl)-3-methyl-butan-2-one (3.720 g, 18.03 mmol) in acetonitrile (40 mL) was added N-iodosuccinimide (5.679 g, 25.24 mmol) and trifluoroacetic acid (0.7 mL, 9.02 mmol) with stirring under argon. The reaction mixture was stirred at room temperature for 10 min then at 50° C. for 1 h. Upon cooling to room temperature, it was diluted with 10% ethyl acetate in hexane and filtered through a bed of Celite and silica gel. The filtrate was washed with water (1×), saturated solution of sodium bicarbonate (1×), 5% solution of sodium thiosulfate (1×), brine (1×), dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the crude residue by flash chromatography (330 g of silica gel, eluting with 30% ethyl acetate in hexane over 30 min) gave 4.83 g of 3-(3-ethoxy-4-iodo-phenyl)-3-methyl-butan-2-one as off-white solid.

Provenance & Evidence