Sodium Azide → 3-Chloro-5-methoxybenzylazide

Participants

Reaction Steps

To a solution of methanesulfonic acid 3-chloro-5-methoxybenzyl ester (20 mmol, 5.01 g) in DMF (30 ml) was added NaN3 (60 mmol, 3.90 g). The mixture was stirred for 3 h and the contents subsequently separated between water (300 ml) and DCM (150 ml). The organic phase was washed with water (2×100 ml), then brine, and dried (MgSO4). Filtration and removal of solvents under reduced pressure yielded a yellow liquid (4.14 g). Purification by means of flash chromatography (silica, hexane/ether gradient 0-50%) provided the title compound (3.65 g, 93%). 1H NMR (CDCl3, 500 MHz) δ 3.80 (s, 3H), 4.27 (s, 2H), 6.73 (s, 1H), 6.85 (s, 1H) and 6.89 (s, 1H).

Provenance & Evidence