Hydrochloric Acid → HCID 18441887, compound

Participants

Reaction Steps

To 120 ml of dichloromethane solution of (2,4-difluorophenyl)acetic acid (10 g, 58.1 mmol) at 0° C., 1,1′-carbonyldiimidazole (9.4 g, 58.1 mmol) was added slowly. The mixture was then stirred for 2.5 hours at room temperature. The solvent was removed. Then the solid residue was triturated with diethyl ether and dried. The white fluffy solid 1-[(2,4-difluorophenyl)acetyl]-1H-imidazole was used for the next step without further purification. In a separate flask, to the 100 ml of dimethyl sulfoxide solution of potassium tert-butoxide (7.2 g, 63.9 mmol) at 0° C., nitromethane (4.6 g, 75.5 mmol) was added. After stirring for 5 minutes, the 1-[(2,4-difluorophenyl)acetyl]-1H-imidazole made previously was added slowly. The mixture was left stirring overnight while the temperature was gradually warmed up to room temperature. The reaction mixture was poured into 250 ml water and then acidified with 2N HCl to pH=4. The aqueous was extracted with ethyl acetate. After washing with brine and drying with sodium sulfate, removal of the solvent afforded 9.4 g yellowish solid. 1H-NMR (400 MHz, CD3OD) δ 7.18 (m, 1H), 6.82 (m, 2H), 5.30 (s, 2H), 3.82 (s, 2H) ppm. ESI-MS m/z 214 (M−H)−.

Provenance & Evidence