5-(2-Bromo-5-fluoro-phenyl)-2-methyl-2H-tetrazole → 4-Fluoro-2-(2-methyl-2H-tetrazol-5-yl)-benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(2-bromo-5-fluoro-phenyl)-2-methyl-2H-tetrazole (650 mg, 2.53 mmol) and CuCN (224 mg, 2.5 mmol) in dimethylformamide (4 mL) was placed in a sealed tube and heated at 100-110° C. for 20 hrs. After cooling, the insoluble material was filtered, and the filtrate concentrated in vacuo. The residue was dissolved in CH2Cl2, washed with aq. 4N HCl and dil. NH4OH, then dried (MgSO4), filtered, and concentrated. The residual solid was purified by column chromatography (SiO2, CH2Cl2) to obtain 375 mg (Yield 73%) of the title compound as an off-white solid; 1H NMR (500 MHz, CDCl3) δ ppm: 4.48 (3H, s) 7.29 (1H, dd, J=7.6, 2.8 Hz) 7.85 (1H, dd, J=8.6, 5.2 Hz) 8.00 (1H, dd, J=9.0, 2.6 Hz); LC/MS m/z 204.

Provenance & Evidence