Methyl iodide → 2-Bromo-5-methoxy-1,3-dimethylbenzene

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-bromo-3,5-dimethyl-phenol (40.2 g, 0.200 mol) and potassium carbonate (55.2 g, 0.400 mol) in acetone (200 mL) was added methyl iodide ( 24.9 mL, 0.600 mol) at room temperature under N2. The reaction mixture was then refluxed at 65° C. for 8 h. After cooling to room temperature, the mixture was filtered, and the filtrate was concentrated in vacuo. The resulting clear liquid was distilled under reduced pressure (70° C./0.1 Torr) to give 42.4 g (99%) of title compound as a colorless liquid. 1H NMR (400 MHz, CDCl3): δ 6.663 (s, 2H), 3.778 (s, 3H), 2.402 (s, 6H); 13C NMR (100 MHz, CDCl3): δ 158.165, 139.203, 118.357, 113.953, 55.520, 24.319. MS (EI): m/z 214 [M+, 79Br 100], 216 [M+, 79Br, 96].

Provenance & Evidence