Methyl iodide → 2-Bromo-1-methoxy-4-(1-methylpropyl)benzene

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Reaction Steps

2-Bromo-4-sec-butyl-phenol (1.50 g) is dissolved in N,N-dimethylformamide (10 ml) and thereto are added potassium carbonate (1.18 g) and iodomethane (1.12 g) and the mixture is stirred at room temperature overnight. Thereto are added ethyl acetate and water, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=1:0→20:1) to give 2-bromo-4-sec-butyl-1-methoxy-benzene (1.58 g). NMR (CDCl3): 0.80 (3H, t), 1.20 (3H, d), 1.55 (2H, m), 2.51 (1H, m), 3.87 (3H, s), 6.82 (1H, d), 7.07 (1H, d), 7.35 (1H, s).

Provenance & Evidence