1-Ethynyl-4-methoxybenzene → 1-(3,5-Dichlorophenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-methoxy-1-ethynyl benzene (0.57 g, 4.27 mmol) in 20 mL of anhydrous THF cooled to −78° C. under a N2 atmosphere was added nButLi (3.2 mL, 5.12 mmol). After 5 minutes a solution of 3,5-dichloro-N-methoxy-N-methylbenzamide (1.0 g, 4.27 mmol) in THF (10 mL) was added to the reaction. The reaction was slowly warmed to 40° C. over 30 minutes and then quenched with saturated NH4Cl solution. The resulting bi-phasic mixture was extracted with EtOAc (3×). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography using 1:10 ethyl acetate-hexanes to give the title compound as a yellow solid. 1H NMR (CDCl3, 500 MHz): δ 8.09 (d, J=2.0 Hz, 2H), 7.7 (d, J=7.1 Hz, 2H), 7.64 (t, J=1.8 Hz, 1H), 7.0 (d, J=8.7 Hz, 1H), 3.91 (s, 3H).

Provenance & Evidence