HCID 58877903, compound → HCID 58877898, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(2-bromo-5-fluorophenyl)-1-methyl-1H-1,2,4-triazole (1.85 g, 7.22 mmol) in N,N-dimethylformamide (10 ml) was treated with copper (I) cyanide (0.71 g, 7.95 mmol). The mixture was then maintained under vacuum for a few minutes, flushed with argon and heated at 100° C. for 16 h. The solvent was then evaporated in vacuo and the residual oil was diluted with ethyl acetate and washed with a solution of 10% ammonium hydroxide followed by 20% ammonium chloride in water. The organic fraction was then washed with brine, dried over anhydrous magnesium sulfate and concentrated. Column chromatography of the residue on silica gel (elution gradient ethyl acetate 0-40% in toluene) gave 1.09 g (75% yield) of the title nitrile as white crystals: mp 134° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 3.98 (3H, s, CH3), 7.37-7.42 (2H, m, aromatics), 7.90 (1H, dd, J=5.0 Hz and J=8.6 Hz, aromatic), 8.08 (1H, s, CH). Anal. Calcd for C10H7FN4: C 59.40, H 3.49, N 27.71; Found: C 59.22, H 3.28, N 27.68.

Provenance & Evidence