Potassium Hydroxide → HCID 9823013, compound

Participants

Reaction Steps

To a solution of [4-(2-bromo-dibenzothiophen-1-yl)-phenoxy]-acetic acid methyl ester (0.449 g, 1.05 mmol) in tetrahydrofuran (15 mL) and methanol (5 mL) was added an aqueous solution of potassium hydroxide (1N, 1.26 mL, 1.2 eq) dropwise at room temperature. After stirring 1 hour at room temperature the solvents were removed and the residue was disolved in water (50 mL) and the reaction mixture was acidified with 10% hydrochloric acid. After stirring 15 minutes the white solid was collected on a sintered glass funnel, washed with water and dried in vacuo at 58° C. overnight to give the title compound as a white solid (0.405 g, 93%); mp 209.5-210.5° C.; NMR (DMSO, d6): δ 13.06 (broad singlet), 8.02 (d, J=8 Hz, 1H), 8.01 (dd, J=8,1 Hz, 1H), 7.82 (d, J=8 Hz, 1H), 7.40 (ddd, J=8,7,1 Hz, 1H), 7.26-7.20 (m, 2H), 7.18=7.07 (m, 3H), 6.54 (d, J=8 Hz, 1H), 4.81 (s, 2H); MS [EI] M*+ m/z=412(98%), 414(100%), 1bromine isotope pattern detected, Anal. Calc. for C20H13BrO3S: C, 58.12, H, 3.17, N, 0.00. Found: C, 57.96, H, 2.95, N, 0.03.

Provenance & Evidence