Benzene, 1-bromo-4-ethynyl- → HCID 67336193, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the intermediate from step A (2.1 g, 11.6 mmol) in anhydrous THF (80 mL) cooled to −78° C. under a N2 atmosphere was added LHMDS (1.0 M solution in THF, 11.6 mL). After 5 minutes a solution of 3,5-dichloro-N-methoxy-N-methyl benzamide (2.71 g, 11.6 mmol) in THF (20 mL) was added to the reaction. The reaction was slowly warmed to 0° 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 bright yellow solid. 1H NMR (CDCl3, 500 MHz): δ 8.07 (d, J=1.8 Hz, 2H), 7.66 (t, J=1.9 Hz, 1H), 7.64 (d, J=8.5 Hz, 2H), 7.6 (d, J=8.7 Hz, 2H).

Provenance & Evidence