Trichloroacetyl chloride → 4,4-Dichloro-3-(4-methylthiophenyl)-2-phenyl-2-cyclobuten-1-one

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Reaction Steps

To a suspension of l-(methylthio)-4-(phenylethynyl)benzene (method 6, 20 g) and Zn(Cu) couple (17.3 g) in anhydrous ether (450 mL) at 15° C. was added trichloroacetyl chloride (32.4 g) dropwise (over 3h). Internal temperature was maintained between 13°-16° C. during addition. The mixture was stirred at r.t. for 18 hr, filtered through a pad of celite®, washed with a saturated NH4Cl sol., saturated NaCHO3 sol., brine, dried (MgSO4) and the solvents evaporated. The resulting residue was first purified by flash chromatography (silica gel; hexane/EtOAc (98:2 to 90:10)) and then the resulting solid was stirred vigorously in Et2O for 3 hr and filtered to afford the title compound as a pale yellow solid, m.p. 99°-100° C.

Provenance & Evidence