Ethanol → Ethyl 2-(5-bromopyridin-3-yl)acetate

Participants

Reaction Conditions

Reaction Steps

To a mixture of ethanol (10 mL) and conc. H2SO4 (4 mL) was added the title compound from Example 53 Step B (0.50 g, 2.5 mmol) in 3 mL of ethanol at room temperature. The mixture was stirred at 90° C. overnight. The reaction was poured into ice and made basic with saturated aqueous sodium bicarbonate solution. It was then extracted with ethyl acetate (2×30 mL), the organic layer was dried, concentrated and purified by flash chromatography on silica gel (petroleum ether:ethyl acetate=10:1) to give the title compound: LCMS m/z 244 [M+H]+; 1H NMR (300 MHz, CDCl3) δ 8.60 (s, 1H), 8.44 (s, 1H), 7.82 (s, 1H), 4.17-4.20 (m, 2H), 3.61 (s, 2H), 1.27-1.30 (m, 3H).

Provenance & Evidence