Ethyl bromodifluoroacetate → HCID 23075290, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere ethylbromodifluoroacetate (0.244 mL, 1.90 mmol) was added to a suspension of 5,6,7,8-tetrahydro-N-(4-iodophenyl)-5,5,8,8-tetramethylnaphthalene-2-carboxamide 22 (826 mg, 1.90 mmol), powder copper (99.999%, 588 mg) in anhydrous DMSO (16.7 mL). The reaction mixture was stirred at 58° C. for 18 h. After cooling, the mixture was poured in aqueous NH4Cl 5% (150 mL). This mixture was extracted with EtOAc (5×150 mL). The organic layer was washed with aqueous NH4Cl 5% (3×100 mL), brine (3×100 mL), dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography using as eluent cyclohexane:EtOAc=95:5. Ethyl 2-(4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)phenyl)-2,2-difluoroacetate 23 was obtained (0.61 g, 74.6% yield) as a white solid.

Provenance & Evidence