Iodoethane → 2-Chloro-5-ethoxy-4-iodopyridine

Participants

Reaction Conditions

Reaction Steps

Treat a solution of 6-chloro-4-iodo-pyridin-3-ol (4.9 g, 19 mmol) and potassium carbonate (8.0 g, 58 mmol) in DMF (50 mL) with ethyl iodide (4.7 mL, 58 mmol). Heat the mixture at 60° C. for 3 h. Cool the mixture to RT and filter through filter paper. Dilute the mixture with ethyl acetate and wash with a 10% aqueous citric acid solution. Combine the aqueous solutions and extract with two additional portions of ethyl acetate. Combine the organic extracts and wash with three portions of water, one portion of saturated aqueous sodium chloride, dry over sodium sulfate, filter, and concentrate in vacuo to give the title compound 5.1 g (93%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 8.00 (s, 1H), 7.93 (s, 1H), 4.18 (q, J=7 Hz, 2H), 1.35 (t, J=7 Hz, 3H).

Provenance & Evidence