Ethyl orthoformate → 3-Bromo-4-(tetrazol-1-yl)anisole

Participants

Reaction Conditions

Reaction Steps

2-Bromo-4-methoxyaniline (1.2 g, 6 mmol; Desc. 7a) was dissolved in glacial acetic acid (10 ml) and heated to 75° C. To this solution was added triethylorthoformate (2.5 ml, 15 mmol) and heated at 75° C. for 1 hour. Sodium azide (1.16 g, 18 mmol) was added portionwise and reaction heated at 75° C. for a further 3 hours and stirred at ambient temperature for 24 hours. The reaction was diluted with water (100 ml) and product extracted into ethyl acetate (3×70 ml). The combined organics were washed with brine (100 ml), dried over magnesium sulphate and the solvent removed in vacuo. Medium pressure chromatography eluting with 40% ethyl acetate/hexane afforded the title compound as a white solid (1.5 g, 90%). 1H NMR (360 MHz, d6 -DMSO) δ 3.88 (3H, s), 7.20 (1H, dd, J 2.7 Hz, J 8.8 Hz), 7.51 (1H, d, J 2.7 Hz), 7.68 (1H, d, J 8.8 Hz), 9.83 (1H, s).

Provenance & Evidence