p-Toluenesulfonic acid → 2-Bromo-4-fluoro-1-(methoxymethoxy)benzene

Participants

Reaction Steps

To a solution of 2-bromo-4-fluoro-phenol (1 g, 5.23 mmol) in CH2Cl2 (120 mL) was added p-toluenesulphonic acid (0.07 g, mmol), dimethoxymethane (2.31 mL, 26.15 mmol) and the resulting mixture was heated under reflux for 16 h under a soxhlett apparatus charged with freshly dried molecular 4 Å sieves. The reaction was allowed to warm to room temperature and washed with 2M sodium hydroxide (100 mL) then dried (Na2SO4), filtered and the solvent was evaporated under vacuum to give title compound as an oil: 0.567 g, 46%. 1H-NMR (CDCl3, 300 MHz) δ7.31 (dd, 1H, J=2.9, 7.9 Hz, ArH), 7.13 (dd, 1H, J=4.9, 9.1 Hz, ArH), 6.98 (m, 1H, ArH), 5.21 (s, 2H, —OCH2O—), 3.54 (s, 3H, —OCH3)

Provenance & Evidence