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

Temperature

93 °C

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.

1. customThe solvent was removed under reduced pressure and chased with methanol
2. customThe residue obtained
3. customwas partitioned between ethyl acetate (25 mL) and 10% sodium bicarbonate solution (25 mL)
4. extractionThe organic phase was extracted with an additional aliquot of 10% sodium bicarbonate solution
5. extractionextracted with ethyl acetate (2×25 mL)
6. dry with materialThe combined organic extracts were dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-eb980f995eda4ea3bb0b252691240784

Source dataset

uspto-grants-1994_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05284954