Acetic Acid → 2-[3-(4-Trifluoromethyl-benzyloxycarbonylmethyl)-phenylsulfanylmethyl]-benzoic acid

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Reaction Steps

2-[3-(4-Trifluoromethyl-benzyloxycarbonylmethyl)-phenylsulfanylmethyl]-benzoic acid 2,2,2-trichloro-ethyl ester (105 mg, 0.177 mmol) was dissolved in DCM (8 mL) and zinc (232 mg, 3.55 mmol) was added. After stirring for 5 minutes HOAc, 97% (1 mL, 18 mmol) was added dropwise. The resulting slurry was stirred for 1.5 h before zinc was filtered off and washed with DCM. The organic phase was washed with water, dried through a phase separator and concentrated. The crude was submitted to flash chromatography using heptane and EtOAc (70/30-60/40) as eluent to give the titled compound (57 mg, 70%) as an oil; 1H NMR (400 MHz, CDCl3): δ 3.64 (s, 2H), 4.56 (s, 2H), 5.18 (s, 2H), 7.09-7.14 (m, 1H), 7.16-7.21 (m, 2H), 7.22-7.34 (m, 3H), 7.36-7.43 (m, 3H), 7.60 (d, 2H), 8.00 (d, 1H); Mass spectrum: M−H+ 459.

Provenance & Evidence