Bromine → 2-Bromo-5,6-dihydrothieno(2,3-c)pyridin-7(4H)-one

Participants

Reaction Conditions

Reaction Steps

Dissolve 5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (4.80 g, 31.37 mmol) in HOAc (40 mL) and water (30 mL). Cool to 0° C. and add Br2 (1.8 mL, 34.51 mmol) dropwise. Stir the reaction at 0° C. for 1 h. Dilute the reaction mixture with water (100 mL) and extract with EtOAc (3×100 mL). Wash the combined organic layers with 5% Na2SO3 (2×50 mL), saturated NaHCO3 (2×100 mL), dry over Na2SO4, filter, and concentrate to give 6.198 g (85%) of the title compound. MS/ES m/z (81Br) 233.9 [M+H]+; 1H-NMR (400 MHz, CDCl3) δ 2.87 (t, J=6.9 Hz, 2H), 3.59 (t, J=6.9 Hz, 2H), 6.21 (bs, 1H), 6.93 (s, 1H).

Provenance & Evidence