Ethanol → HCID 66718910, compound

Participants

Reaction Steps

To a solution of 4-bromo-1-(bromomethyl)-2-fluorobenzene (56.0 mmol) in ethanol (75.0 ml) and water (15.0 ml) was added sodium cyanide (67.2 mmol). The reaction was refluxed for 3 days then cooled and diluted with water. The solids were collected, slurried in water (100 mL) and 6N aq HCl (50 mL) for 1 h, and then filtered and dried via suction. The collected solids were slurried again in dichloromethane, and the solids were collected and dried to afford 2-(4-bromo-2-fluorophenyl)acetamide (6.9 g, 52% yield) as a white solid. The dichloromethane filtrate was evaporated to afford a crude mixture (72% purity by LCMS) of the title product and 2-(4-bromo-2-fluorophenyl)acetamide (1.4:1 ratio) as a light yellow solid (4.5 g). A portion of this mixture was used directly in the next step. Title product: MS(ES)+ m/e 214.0, 216.2 [M+H]+.

Provenance & Evidence