4-Toluenesulfonyl chloride → HCID 86586227, compound

Participants

Reaction Conditions

Reaction Steps

p-Toluenesulfonylchloride (2.14 g, 11.2 mmoles) was added to a solution of 4-bromoresorcinol (2.12 g, 11.2 mmoles) and K2CO3 (10.0 g, 72.4 mmoles) in acetone (150 mL). The reaction was heated to 60° C. overnight, treated with allyl bromide (2.6 mL, 30.3 mmoles), and heated to 60° C. for 24 h (according to Bos, M. E.; Wulff, W. D.; Miller, R. A.; Chamberlin, S.; Brandvoid, T. A. J. Am. Chem. Soc. 1991, 113, 9293). The reaction was cooled to room temperature, quenched with aqueous NH4Cl, and concentrated under reduced pressure. The crude products were diluted with diethyl ether, extracted with H2O, washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography on a prepacked Biotage colum (hexane to 4:1 hexane:ethyl acetate) on silica gel to provide the title compound (3.50 g, 81%) as a clear colorless oil.

Provenance & Evidence