Sodium Bicarbonate → Methyl 5-bromobenzo[d][1,3]dioxole-4-carboxylate

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Reaction Steps

5-Bromo-1,3-benzodioxole-4-carboxylic acid (0.34 g, 1.39 mmol) was dissolved in methanol (25 mL). A few drops of concentrated sulfuric acid were added and the solution was heated to reflux for 60 h at which time TLC analysis indicated the reaction complete. The reaction was cooled and poured into a solution of 5% NaHCO3 (25 mL) and extracted with ethyl acetate. The organic layers were dried with magnesium sulfate and concentrated by rotary evaporation to afford 0.20 g of product (0.77 mmol, 55% yield) as an off-white solid. 1H NMR (CDCl3) δ 7.11 (d, J=8.3 Hz, 1H), 6.78 (d, J=8.3 Hz, 1H), 6.09 (s, 2H), 3.95 (s, 3H).

Provenance & Evidence