Hydrochloric Acid → HCID 914663, compound

Participants

Reaction Steps

To a solution of 5-bromo-1-methyl-1H-imidazole (10 g, 62 mmol) in dichloromethane (50 mL) was added dropwise ethylmagnesium bromide (3 M in Et2O, 20.7 mL, 62 mmol). After stirring at room temperature for 15 min, the reaction mixture was cooled down to 0° C. with an ice-brine bath and N-methoxy-N-methylbenzamide (9.46 mL, 62 mmol) was added dropwise. The mixture was stirred for 2 h at room temperature. After standing for one night at room temperature, the mixture is worked-up by addition of water (150 mL), then acidified with aq. HCl (1 M) until pH=7. After extraction with dichloromethane (2×100 mL), the organic layers were washed with water (100 mL) then dried over MgSO4 and concentrated in vacuo. The resulting orange solid was washed with pentane to afford (1-methyl-1H-imidazol-5-yl)(phenyl)methanone [8.50 g, yield 66%; HPLC/MS: m/z=187 (M+H); log P(HCOOH)=0.79].

Provenance & Evidence