Dichloromethane → 2-Amino-3-bromo-5-methylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

The (2-amino-3-bromo-5-methylphenyl)methanol (7.80 g, 36.1 mmol) was dissolved in tetrahydrofuran (20 mL). Dichloromethane (50 mL) was added along with activated carbon (16.3 g). Manganese dioxide (9.4 g, 108 mmol) was added and the solution stirred at 40° C. for 16 h. The solution was cooled to room temperature and vacuum filtered through a celite. The solvent was removed at reduced pressure and the 2-amino-3-bromo-5-methylbenzaldehyde (6.10 g, 28.5 mmol) obtained by recrystallization from diethyl ether/hexanes (1:10, 100 mL) (78% yield): Melting point 99.6-101.2° C. 1H NMR (300 MHz, CDCL3) 9.77 (s, 1H), 7.46 (s, 1H), 7.26 (s, 1H), 6.48 (bs, 2H), 2.76 (s, 3H). HRMS m/z 213.9902; calcd for M+H 213.9962.

Provenance & Evidence