N-(4-Bromo-2-fluoro-benzyl)-2-methoxy-4-methylsulfanyl-benzamide → N-(4-bromo-2-fluoro-benzyl)-2-hydroxy-4-methylsulfanyl-benzamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-(4-bromo-2-fluoro-benzyl)-2-methoxy-4-methylsulfanyl-benzamide (11 g crude, from step 1) was dissolved in a 25% HBr in glacial acetic acid solution (400 mL) and heated to 100° C. for 4 h. The solution was diluted with ethyl acetate (750 mL) and washed with saturated NaCl (500 mL). The organic layer was dried over MgSO4, filtered and concentrated. Purification by MPLC (10–100% ethyl acetate in heptane, 23 mL/min, 75 min) gave N-(4-bromo-2-fluoro-benzyl)-2-hydroxy-4-methylsulfanyl-benzamide (5.0 g, 50%). Rf 0.57 (40% ethyl acetate in heptane); 1H NMR (DMSO-d6 300 MHz) δ 12.57 (s, 1 H), 9.22 (t, J=5.4 Hz, 1 H), 7.78 (d, J=8.4 Hz, 1 H), 7.52 (dd, J, =9.8 Hz, J2=1.7 Hz, 1 H), 7.40–7.27 (m, 2 H), 6.77–6.71 (m, 2 H), 4.46 (d, J=5.7 Hz, 2 H), 2.46 (s, 3 H).

Provenance & Evidence