Diethyl Ether → 2,3-Dichloro-1,4-benzoquinone

Participants

Reaction Steps

To a solution of 1,4-benzoquinone Q-4 (2.0 g, 18.52 mmol) in diethyl ether-chloroform (4:1, 90 mL) at 0° C. and under N2 atmosphere was added sulfuryl chloride (3.0 mL, 37.0 mmol) dropwise over a period of 30 min. The reaction mixture was poured onto crushed ice, and extracted with diethyl ether (3×100 mL). Silver (I) oxide (10 g, 43.15 mmol) was added to the combined diethyl ether layers and the mixture was stirred for 1 h. After filtration, the filtrate was concentrated in vacuo to obtain crude Q-6, which was purified by column chromatography (silica gel, 10% ethyl acetate-pet. ether) to afford compound Q-6 (2.3 g, 71%) as a pale yellow solid. TLC Rf=0.6 (petroleum ether-EtOAc, 9:1); MS (ES) m/z 176 (M−H)−.

Provenance & Evidence