Water → 3-Bromo-2,5-dimethoxybenzaldehyde

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A solution of 50 (10 g, 43 mmol), Methyl Iodide (7.3 g, 52 mmol), and K2CO3 (12 g, 86 mmol) in acetone (200 ml) was heated to reflux. After 4 hr, the reaction was cooled, poured into water and extracted with ether. The ether layer was dried concentrated and the product was purified by silica gel column chromatography (10%EtOAc/Hex) to give 51 as a solid (7.0 g, 67%): Mp=62-64° C.; 1H NMR (CDCl3) δ 10.32 (s, 1 H), 7.38 (d, 1 H, J=2.8 Hz), 7.28 (d, 1 H, J=3.2 Hz), 3.93 (s, 3 H), 3.82 (s, 3 H); MS 245/247 (M+H)+

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