Methyl iodide → HCID 58071403, compound

Participants

Reaction Conditions

Reaction Steps

To a homogeneous CH3CN (200 mL) solution of 4,6-dibromo-2-fluoro-3-methylphenol (2, 28.4 g, 100 mmol) at rt, K2CO3 (16.59 g, 120 mmol) was added, followed by MeI (9.3 mL, 150 mmol). The cloudy solution was stirred at 30° C. overnight. The reaction went to completion monitored by LC and TLC. The mixture was cooled to rt, quenched by addition of H2O (100 mL) and sat. aq. NH4Cl (100 mL), two layers were mixed well and then separated, aqueous layer was extracted with EtOAc (50 mL), organic layers were combined, dried (MgSO4), filtered, solvent was removed in vacuo. The crude product, an oil, was dissolved in CH2Cl2 (˜80 mL) and the solution was passed through a silica gel pad (˜50 g of silica gel), washing with CH2Cl2 (˜100 mL). The filtrate was collected, and the solvent was removed in vacuo. 1,5-Dibromo-3-fluoro-2-methoxy-4-methylbenzene was obtained as a solid: 31.62 g (>99% yield); 1H NMR (300 MHz, CDCl3) δ 7.53 (d, J=2.1, 1H), 3.92 (s, 3H), 2.29 (d, J=2.8, 3H).

Provenance & Evidence