Dimethylformamide → HCID 67055850, compound

Participants

Reaction Steps

To a stirred solution of 2-(1-(3,3-dimethylbutyl)-1H-imidazol-5-yl)phenol (122.0 mg, 0.5 mmol) in DMF (3 mL) at 0° C. was added NaH (36.0 mg, 0.75 mmol) portion wise. The resulting mixture was allowed to stir for 10 min and 1-(bromomethyl)-4-chlorobenzene (123.0 mg, 0.6 mmol) was added. After stirring overnight the reaction mixture was diluted with water and the aqueous phase extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with water, brine, dried (Na2SO4) and concentrated under reduced pressure to afford the crude residue, which was purified by column chromatography on silica gel to afford the desired product in 30% yield. 1H NMR: 0.78 (s, 9H), 1.38-1.47 (m, 2H), 3.75-3.85 (m, 2H), 5.00 (s, 2H), 6.98-7.09 (m, 3H), 7.15 (d, 2H, J=7.6 Hz), 7.24-7.40 (m, 4H), 7.55 (s, 1H).

Provenance & Evidence