Acetic Acid → HCID 18439772, compound

Participants

Reaction Steps

A solution of 2-bromo-3′-methoxyacetophenone (40.0 g, 0.18 mol) and thiazolidinedione (24.5 g, 0.21 mol) in dry DMF (175 mL) was treated with K2CO3 (36.2 g, 0.26 mol) and stirred at RT for 1.5 h. The reaction mixture was slowly poured into ice water (1.7 L). The resulting pink solid, was collected by filtration and washed with water (200 mL). (Excess water was removed by suction) The filter cake was stirred at RT for 30 min in an aqueous solution (350 mL),of lithium hydroxide-hydrate (29.3 g, 0.7 mol) and THF (350 mL). After ice water (700 mL) was added, the suspension was slowly poured into a stirred solution of acetic acid (40 mL, 0.70 mol) in water (1.7 L). The resulting tan solid was collected by filtration, washed with water (500 mL), and dried under vacuum to afford the title compound (23.8 g, 72%). 1H NMR (300 MHz, d6-DMSO): δ 3.80 (s, 3H), 6.86 (dd, 1H, J1=8.1, J2=2.4 Hz), 7.05 (bs, 1H), 7.09 (d, 1H, J=7.8), 7.33 (t, 1H, J=8.1), 7.54 (s, 1H).

Provenance & Evidence