Fluoride Ion → 4-(2,6-difluorophenyl)-1H-1,2,3-triazole-5-carbonitrile

Participants

Reaction Steps

4-(2,6-difluorophenyl)-1H-1,2,3-triazole-5-carbonitrile (2) was prepared in one step from 2,6-difluorobenzaldehyde (1) and nitroacetonitrile using a modified literature procedure (see Fringuelli et al. Eur. J. Org. Chem. (2008) 3928-3932). A solution of 2,6-difluorobenzaldehyde (1.0 equiv), nitroacetonitrile (1.5 equiv) and TMS-azide (3.0 equiv) in dry THF (0.4 M) under inert atmosphere and at 0° C. was treated with fluoride-bound resin (Aldrich #387789, 1:1 w/w with respect to aldehyde). The resulting mixture was heated to reflux for 2 h (reaction completed according to TLC), cooled to room temperature and concentrated in vacuo to provide (2) as an orange solid which was used directly in the next reaction.

Provenance & Evidence