Potassium Hydroxide → HCID 22093448, compound

Participants

Reaction Steps

A solution of [4-hydroxy-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid ethyl ester (0.773 g, 1.83 mmol)in ethanol (10 mL, 0.18 M) was cooled to 0° C. and treated with aq KOH (5 mL, 1.25 M) and warmed to room temperature. The solution was acidified to pH 1–2, diluted with ethyl acetate and washed with sat'd aq NaCL. The organic layer was dried over Na2SO4, filtered and concentrated to give [4-hydroxy-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid as a white crystaline solid: mp 244 dec.; 1H NMR (DMSO-d6, 300 MHz) δ 10.14 (br s, 1 H), 8.97 (t, J=5.4 Hz, 1 H), 7.75 (dd, J1=8.4 Hz, J2=0.3 Hz, 1 H), 7.48 (d, J=9.6 Hz, 1 H), 7.37–7.26 (m, 2 H), 6.46 (dd, J1=8.7 Hz, J2=2.1 Hz, 1 H), 6.40 (s, 1 H), 4.77 (s, 2 H), 4.47 (d, J=5.4 Hz, 2 Hz). Anal. calcd for C16H13BrFNO5: C, 48.26; H, 3.29; N, 3.52. Found C, 48.19; H, 3.52; N, 3.32.

Provenance & Evidence