[Synthesis]
Sodium azide (520 mg, 8.0 mmol) was added to DMSO (20 mL) and stirred
vigorously until it had dissolved fully. 2-Nitrobenzyl bromide 171 (1.728
g, 8.00 mmol) was added, and the reaction was allowed to stir overnight.
The reaction mixture was diluted with water (20 mL) and then extracted
with diethyl ether (3 x 30 mL). The combined organics were washed with
water (30 mL) and brine (30 mL), dried over sodium sulphate, and after
filtration, evaporated to dryness under reduced pressure. 2-Nitrobenzyl
azide 124 was obtained as an orange oil (1.341 g, 7.53 mmol, 94%): IR
(neat) νm a x / cm– 1 3455, 3016, 2970, 2946, 2101, 1738, 1611, 1578, 1523,
1445, 1353, 1293, 1228, 1217, 857, 788, 730; 1H NMR (400 MHz, CDCl 3 ) δ
8.12 (d, J = 7.9 Hz, 1H), 7.73 – 7.64 (m, 2H), 7.55 – 7.48 (m, 1H), 4.85 (s,
2H); 1 3C NMR (101 MHz, CDCl 3 ) δ 167.23, 134.22, 131.78, 130.31, 129.23,
125.49, 52.18. |