tert-Butyl methyl ether → 1,3-Benzodioxole, 5-methoxy-

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Reaction Steps

To a solution of methyl-2-methylbenzoate (3.00 g, 20.0 mmol) in carbon tetrachloride (15 ml) was added N-bromosuccinimide (3.55 g. 20.00 mmol). The reaction was allowed to stir at reflux for 3 h. The mixture was cooled and then partioned between t-butyl methyl ether and 5% NaHCO3. The combined organic extracts (×3) were washed with water, brine, and dried (MgSO4). Removal of the solvent under reduced pressure afforded the title compound as a white solid (4.60 g, quantitative yield). 1H NMR (400 MHz. CDCl13) δ 7.98 (d, 1H), 7.54-7.35 (mm, 3H), 4.98 (s, 2H), 3.98 (s. 3H)

Provenance & Evidence