Acetic Acid → HCID 67041568, compound

Participants

Reaction Steps

45% hydrogen bromide in acetic acid (26 μL, 0.20 mmol) was added to a stirring mixture of methyl 4-(4-(benzyloxy)-3-chloro-5-(cyclohexyloxy)benzamido)benzoate (6) (20 mg, 40 μmol) in TFA (3 mL) and the mixture was stirred at RT for 1 h. The mixture was partitioned between water (15 mL) and EtOAc (15 mL) and the phases were separated. The organic solution was washed with water (10 mL), dried over MgSO4 and the solvent was removed in vacuo to give methyl 4-(3-chloro-5-(cyclohexyloxy)-4-hydroxybenzamido)benzoate (7) (16 mg, 92%): m/z 402 [M−H]− (ES−); 1H NMR (400-MHz, DMSO-d6) δ: 10.37 (1H, s), 7.94 (4H, m), 7.68 (1H, d), 7.54 (1H, d), 4.40 (1H, m), 3.84 (3H, s), 1.94 (2H, m), 1.83-1.73 (2H, m), 1.57-1.45 (3H, m), 1.40-1.20 (3H, m).

Provenance & Evidence