Diethyl Ether → 6-Bromonaphthalene-2-carbaldehyde

Participants

Reaction Steps

To a suspension of pyridinium chlorochromate (2.4 gr, 11 mmol) in anhydrous CH2Cl2 (60 mL) was added a solution of the above alcohol in anh. CH2Cl2 and the reaction was heated under reflux for 5 hours. Upon completion, it was cooled to room temperature and poured into diethyl ether. The solution was then filtered through a pad of silica and concentrated under reduced pressure to yield 21 (2.4 gr, 95%). 20: white solid; 1H NMR (400 MHz, CDCl3) δ 10.15 (s, 1H), 8.31 (bs, 1H), 8.08 (bs, 1H), 7.98 (dd, 1H, J=1.5 Hz, J=8.5 Hz), 7.86 (m, 2H), 7.67 (dd, 1H, J=1.5 Hz, J=8.5 Hz); 13C NMR (100 MHz, CDCl3) δ 191.8, 137.3, 134.3, 134.1, 131.0, 131.0, 130.6, 130.2, 128.2, 124.0, 123.

Provenance & Evidence