Dichloromethane → Ethanone, 2-bromo-1-tetrazolo[1,5-a]pyridin-6-yl-

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Reaction Steps

6-Acetyl tetrazolo[1,5-a] pyridine (10 g, 62 mmol) in acetic acid (160 mL) was treated with 30% HBr/acetic acid (14.7 mL, 247 mmol) at 0° C. N-bromosuccinimide (11 g, 62 mmol) was slowly added and the reaction stirred for 30 minutes. Another 4 equivalents of 30% HBr/acetic acid (14.7 mL, 247 mmol) was slowly added and the reaction was allowed to warm to room temperature. After 3 hours, the reaction was diluted with ethyl acetate (500 mL) and washed with water (3×300 mL). The organic layer was dried (MgSO4), filtered, and concentrated to afford an oil. Hexanes (75 mL) and dichloromethane (10 mL) were added to the oil and reconcentrated to afford a yellow solid (12.8 9, 86%). Rf =0.2 (CH2Cl2); mp 108-110° C.; 1H NMR (300 MHz, CDCl3) δ 10.2 (s, 1 H), 8.29 (dd, J=9, 10 Hz, 1 H), 8.18 (dd, J=8, 10 Hz, 1 H), 5.06 (s, 2 H); MS (EI) m/z 241 (M+).

Provenance & Evidence