Hydrochloric Acid → HCID 68823443, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(4-chloro-2-fluorophenyl)acetamide (30.0 g, 147 mmol) in THF (300 mL) at −70° C. is added dropwise (keeping the reaction temperature below −60° C.) n-BuLi (2.0 M in cyclohexane, 147 mL, 294 mmol). The reaction is stirred between −60 to −70° C. for 2 hours and 1,1,1-trifluoro-2-iodoethane (46.2 g, 220 mmol) is added dropwise at −70° C. The reaction mixture is stirred at this temperature for additional 1.5 hours before 3N HCl (108 mL) solution is added slowly. The mixture is allowed to warm up to room temperature and extracted with EtOAc (200 mL×3). The organic layers are combined washed with water, brine and then dried over MgSO4. The solvents are removed and the residue is stirred in ether and hexanes (1:2, 120 mL) for 1 hour. A solid precipitate is filtered to give N-(2,4-dichloro-3-iodophenyl)acetamide.

Provenance & Evidence