Phenol → HCID 86607510, compound

Participants

Reaction Steps

A solution of 5-bromo-3-methyl-thiophene-2-carbaldehyde (example 1.a, 30.8 g, 150 mmol), phenol (28.2 g, 300 mmol), cesium carbonate (97 g, 300 mmol), copper(I) trifuoromethanesulfonate benzene complex (90%, 7.5 g, 15 mmol), and ethyl acetate (750 μL, 7.5 mmol) in 150 mL of anhydrous toluene was heated at reflux temperature for 48 hours. The resultant mixture was diluted with dichloromethane and 2 N NaOH(aq) and filtered through a small pad of celite, the solid was washed with additional dichloromethane and NaOH solution. The biphasic mixture was separated and the organic fraction was successively washed with 2 N NaOH and brine. The organic fraction was dried over anhydrous magnesium sulfate and concentrated to a residue. The crude product was purified by column chromatography, eluting the desired product from silica gel with a gradient of 5-30% ethyl acetate in hexanes to provide 6.4 g of product; MS: (+) m/z 219.4 (M+1)

Provenance & Evidence