Water → HCID 20621501, compound

Participants

Reaction Steps

(R)-N-[4-Iodo-2,3-dichlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 4) (4.58 g, 10.7 mmol) was heated in DMF (30 ml) with stirring under argon for 4 hours with 4-mercaptobenzoic acid (2.31 g, 14.98 mmol) and cuprous oxide (765 mg) and allowed to cool to room temp. EtOAc and water were added, and the reaction mixture was filtered through a bed of diatomaceous earth, and washed with EtOAc/water. The organic layer was separated, washed with water, brine, dried and evaporated down to dryness. The resulting solid was purified using a Mega Bond Elut column, eluting with 5-50% EtOAc/isohexane to give the title compound (4.0 g) as a pale pink solid. NMR: 1.6 (s, 3H), 7.3 (d, 2H), 7.5 (d, 1H), 7.9 (m, 3H), 8.0 (d, 1H), 9.9 (s, 1H), 13.0 (s, 1H); m/z: 452.

Provenance & Evidence