Water → (1,1'-Biphenyl)-4-carboxylic acid

Participants

Reaction Steps

LiI (0.042 g, 0.32 mmol) was added to a solution of methyl 3-chloro-3′-((2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)biphenyl-4-carboxylate (0.158 g, 0.32 mmol) in pyridine (5 mL). The reaction mixture was refluxed for 12 h, and then cooled to room temperature. Excess solvent was removed under vacuum. The product was purified by HPLC using isopropanol:water as the solvent system to afford 3-chloro-3′-(2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)biphenyl-4-carboxylic acid as a colorless solid (70 mg, 46% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.01 (s, 1H), 7.82 (d, 1H, J=8.5 Hz), 7.80 (d, 1H, J=8.6 Hz), 7.71-7.76 (m, 4H), 7.49-7.47 (m, 2H), 7.05 (d, 1H, J=8.5 Hz), 5.23 (s, 2H), 4.83-4.81 (m, 1H), 2.02-1.99 (m, 21-1), 1.62-1.60 (m, 6H). LC-MS (ESI) Calcd for C26H22ClNO4S [M+H]+: 480.09. Found: 479.95. HRMS (ESI) calcd for C26H22ClNO4S [M+H]+: 480.1031. Found: 480.1031.

Provenance & Evidence