2-Bromobenzonitrile → 5-(2-Bromophenyl)-1H-tetrazole

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Reaction Conditions

Reaction Steps

A mixture of 2-cyanophenyl bromide (1.00 g, 5.49 mmol), dibutyltin oxide (90.4 mg, 0.549 mmol) and trimethylsilyl azide (1.26 g, 10.98 mmol) in toluene (10.9 mL) were heated at 93° C. for 72 hours. The solvent was removed under reduced pressure and chased with methanol. The residue obtained was partitioned between ethyl acetate (25 mL) and 10% sodium bicarbonate solution (25 mL). The organic phase was extracted with an additional aliquot of 10% sodium bicarbonate solution. The combined aqueous extracts were acidified to pH 2 with 10% hydrochloric acid and extracted with ethyl acetate (2×25 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to give the title compound (190 mg. 74%) as a white solid. 1H NMR (CD3OD, 300 MHz) δ7.48-7.6 (m, 2H), 7.70 (dd, J=2 Hz, 7 Hz, 1H), 7.84 (dd, J=1 Hz, 6 Hz, 1H). HRMS (DCl/NH3) m/e, calcd for C7H6N479Br: 224.9776, found 224.9762. IR (KBr) 3440, 2600, 1602, 1056, 748 cm-1. Anal calc for C7H6N4Br: C, 37.36; H, 2.24; N, 24.90. Found: C, 37.44; H, 2.25; N, 24.77.

Provenance & Evidence