Potassium Carbonate → 4-[[4-[(4-Trifluoromethylphenoxy)methyl]phenyl]sulfanyl]-2-methylphenoxy-acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

An oven-dried 500 mL round-bottomed flask was charged with crude 7.3 (prepared from 7.2 (30.0 g, 90.2 mmol)) and DMF (200 mL) and cooled to 0° C. Next, 4-hydroxybenzotrifluoride (17.5 g, 108 mmol) and K2CO3 (24.9 g, 180 mmol) were added at 0° C., and the reaction heated to 70-80° C. and stirred for 2 h. The reaction mixture was poured into ice-water (400 mL), and the product was extracted with toluene (400 mL). The organic layer was successively washed with water (2×300 mL) and brine (400 mL), dried over MgSO4, and concentrated to give a slightly yellow oil which was purified by flash chromatography (SiO2 gel 60 N, eluted with AcOEt/hexane=⅙). The fractions containing only desired product were combined and concentrated to a slightly yellow oil (40.9 g). 1H NMR (400 MHz) (CDCl3) δ 7.53 (2H, d, J=8.6 Hz); 7.30-7.20 (4H, m); 7.17 (2H, d, J=8.4 Hz); 7.00 (2H, d, J=8.7 Hz); 6.68 (1H, d, J=8.4 Hz); 5.04 (2H, s); 4.66 (2H, s); 4.27 (2H, q, J=7.1 Hz); 2.27 (3H, s); 1.30 (3H, t, J=7.1 Hz).

Provenance & Evidence