(6-Bromonaphthalen-2-yl)methanol → 6-Bromonaphthalene-2-carbaldehyde

Participants

Reaction Steps

To a three-necked flask (250 ml) was added (6-bromonaphthalen-2-yl)methanol (40.0 g, 0.170 mol) and dichloromethane (1.6 L) with magnetic stirring under nitrogen to form a clear solution. To this solution, Pyridinium chlorochromate (40.0 g, 0.186 mol) was added, and the resulting mixture turned black at once. Stirring was continued for 1 hour. The mixture was filtered through a short silica gel column, eluted with dichloromethane; the filtrate was dried over anhydrous magnesium sulphate, and then filtered under reduced pressure. The solvent was removed to afford a light brown solid, which was recrystallized from ethanol-water solution (50%) to afford a white solid 6-bromo-2-naphthaldehyde (31 g).

Provenance & Evidence