Hydrochloric Acid → 3-Bromo-6-fluoro-2-methylbenzenamine

Participants

Reaction Conditions

Reaction Steps

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was charged with 1-bromo-4-fluoro-2-methyl-3-nitrobenzene (700 mg, 2.58 mmol), tin(11) chloride dihydrate (2.62 g, 11.6 mmol), hydrochloric acid (6.5 mL) and methanol (6.5 mL), and the reaction mixture was heated at 40° C. for 2 h. After this time, potassium carbonate was added to adjust the pH of the solution to 12, and the resulting suspension was extracted with methylene chloride (2×50 mL). The organic extracts were combined and dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography to afford 3-bromo-6-fluoro-2-methylaniline in a 98% yield (598 mg) as a yellow solid: mp 49-50° C.; 1H NMR (500 MHz, CDCl3) δ 6.91 (dd, 1H, T=9.0, 5.0 Hz), 6.76 (dd, 1H, J=10.0, 9.0 Hz), 3.77 (bs, 2H), 2.28 (s, 3H); MS (ESI+) m/z 203.9 (M+H).

Provenance & Evidence