Diethyl Ether → 6-Bromonaphthalene-2-carbaldehyde

Participants

Reaction Steps

To a solution of 6-bromo-2-naphthylmethyl alcohol (6.71 g, 28.3 mmol) in CH2Cl2 (350 mL) was added pyridinium chlorochromate (6.71 g, 31.13 mmol) all at once. The mixture visually went from orange-red to black over 30 minutes and 150 mL of ether was added. The black mixture was passed through a silica gel column and eluted with ether. The solvents were evaporated and the solid was further purified on silica gel (hexane:CH2Cl2 1:1) to give 6.25 g of 6-bromo-2-naphthaldehyde (94%) as a white solid. %). 1H NMR (300 MHz; CDCl3): δ 7.65 (dd, J1=2.0 Hz, J2=9.0 Hz, 1H); 7.84 (t, J=8.0 Hz, 2H); 7.97 (dd, J1=2.0 Hz, J2=8.0 Hz, 1H); 8.06 (d, J=2.0 Hz, 1H); 8.29 (s, 1H); 10.14 (s, 1H); 13C NMR (300 MHz; CDCl3): ppm 123.5, 123.9, 128.0, 130.1, 130.5, 130.8, 130.9, 133.9, 134.2, 137.1, 191.6.

Provenance & Evidence