4-(1,2,4-Triazol-1-ylmethyl)benzonitrile → 1-[1-(4-Cyanophenyl)-4-(4-fluorophenyl)butyl]-1,2,4-triazole

HRID 1737859Notes

Reaction equation

HRID 1737859 reaction equation
[C:1]([C:3]1[CH:14]=[CH:13][C:6]([CH2:7][N:8]2[CH:12]=[N:11][CH:10]=[N:9]2)=[CH:5][CH:4]=1)#[N:2].[Li]CCCC.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29]Br)=[CH:23][CH:22]=1>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:7]([N:8]2[CH:12]=[N:11][CH:10]=[N:9]2)[CH2:29][CH2:28][CH2:27][C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)=[CH:13][CH:14]=1)#[N:2]

Participants

4

Reactant 3

HCID 75376164-(1,2,4-Triazol-1-ylmethyl)benzonitrileHCID 147371331-(3-Bromopropyl)-4-fluorobenzeneHCID 178418339Butyllithium

Product 1

HCID 107580381-[1-(4-Cyanophenyl)-4-(4-fluorophenyl)butyl]-1,2,4-triazole

Procedure

The compound is prepared by the method described in Example 1 starting from 1-(4-cyanobenzyl)-1,2,4-triazole (6.0 g, 0.0272 mol), n-BuLi (0.0272 mol) and 3-(4-fluorophenyl)propylbromide (7.6 g, 0.035 mol). The product is purified first by suspending the residue with 2 M aqueous hydrogen chloride and petrol ether. Petrol ether phase is separated and the aqueous layer and the separated oil are extracted with diethyl ether. Diethyl ether phase is evaporated and the residue is purified by flash chromatography.

Workup

  1. customThe compound is prepared by the method
  2. customThe product is purified first
  3. customPetrol ether phase is separated
  4. extractionthe aqueous layer and the separated oil are extracted with diethyl ether
  5. customDiethyl ether phase is evaporated
  6. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-670431ad6d644362ad564db62466aa3c
Source dataset
uspto-grants-1999_10
Patent number
US05962495

Reaction notes

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