Methyl vinyl ketone → 4-(2,4,6-Trichlorophenyl)but-3-en-2-one

Participants

Reaction Conditions

Reaction Steps

A round bottom flask equipped with magnetic stirrer and nitrogen inlet was charged with but-3-en-2-one (1.14 g, 16.25 mmol), 1,3,5-trichloro-2-iodo-benzene (2.0 g, 6.5 mmol), Pd(OAc)2 (125 mg, 0.65 mmol), sodium hydrogen carbonate (1.64 g, 19.5 mmol) and tetrabutylammonium chloride (2.17 g, 7.8 mmol) in DMF (20 ml). The mixture was stirred at 50° C. for 24 hours. The reaction mixture was poured onto water (100 ml) and extracted with ether (3×50 ml). Combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography over silica gel (150 g) (eluent: n-hexane/ethyl acetate 1:20) to afford 1.02 g (63% of theory) of (E)-4-(2,4,6-trichloro-phenyl)-but-3-en-2-one in form of an oil.

Provenance & Evidence