5-Bromo-2-fluoro-3-methylbenzyl alcohol → 5-Bromo-2-fluoro-3-methylbenzaldehyde

Participants

Reaction Steps

To a stirred suspension of pyridinium chlorochromate (3.77 g, 17.1 mmol) and silica gel in 25 ml dichloromethane was added a solution of (5-bromo-2-fluoro-3-methylphenyl)methanol in 25 mL dichloromethane. The reaction was stirred for 30 minutes at room temperature. Added additional silica gel and concentrated to adsorb reaction products onto the silica gel. Flash chromatographed (80 g silica, 5-10% ethyl acetate/hexanes gradient) to yield 2.1 g of 5-bromo-2-fluoro-3-methylbenzaldehyde as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.31 (d, J=2.15 Hz, 3 H) 7.42-7.63 (m, 1 H) 7.77 (dd, J=5.46, 2.34 Hz, 1 H) 10.27 (s, 1 H).

Provenance & Evidence