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

HRID 2097671Notes

Reaction equation

HRID 2097671 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=O.[N+:11]([CH2:14][C:15]#[N:16])([O-])=O.[Si]([N:21]=[N+:22]=[N-])(C)(C)C.[F-]>C1COCC1>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[C:4]1[N:21]=[N:22][NH:11][C:14]=1[C:15]#[N:16]

Participants

6

Reactant 4

HCID 28179Fluoride IonHCID 78378AzidotrimethylsilaneHCID 1362842,6-Difluorobenzaldehyde2×HCID 542681NoName_16612×

Product 1

HCID 1785106704-(2,6-difluorophenyl)-1H-1,2,3-triazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 h
  3. custom(reaction completed according to TLC)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b1a2f294234d4ad387cd4a44add1035e
Source dataset
uspto-grants-2013_05
Patent number
US08450350B2

Reaction notes

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