1H-1,2,3-Triazole → 2,3-difluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid

HRID 1750538Notes

Reaction equation

HRID 1750538 reaction equation
N1N(C2C=CC(C(F)(F)F)=CC=2C(O)=O)N=CC=1.N1(C2C=CC(C(F)(F)F)=CC=2C(O)=O)C=CN=N1.[N:37]1[NH:38][N:39]=[CH:40][CH:41]=1.[F:42][C:43]1[C:51]([F:52])=[CH:50][CH:49]=[C:48](I)[C:44]=1[C:45]([OH:47])=[O:46]>O1CCOCC1.O>[F:42][C:43]1[C:51]([F:52])=[CH:50][CH:49]=[C:48]([N:38]2[N:39]=[CH:40][CH:41]=[N:37]2)[C:44]=1[C:45]([OH:47])=[O:46]

Participants

7

Reactant 4

HCID 675161H-1,2,3-TriazoleHCID 161253052,3-Difluoro-6-iodobenzoic acidHCID 679821772-(2H-1,2,3-triazol-2-yl)-5-(trifluoromethyl)benzoic acid2×HCID 1183081042-(1H-1,2,3-triazol-1-yl)-5-(trifluoromethyl)benzoic acid2×

Product 1

HCID 1177278842,3-difluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Prepared according to the procedure for 2-(2H-1,2,3-triazol-2-yl)-5-(trifluoromethyl)benzoic acid (Intermediate 37a) and 2-(1H-1,2,3-triazol-1-yl)-5-(trifluoromethyl)benzoic acid (Intermediate 37b) from 2H-1,2,3-triazole (CAS number 288-36-8; 0.75 g, 10.86 mmol) and 2,3-difluoro-6-iodobenzoic acid (CAS number 333780-75-9; 1.54 g, 5.43 mmol) in 1,4-dioxane (10 ml) and water (0.2 ml). The crude solid was purified by column chromatography (silica, 0-3% methanol/DCM) to afford 2,3-difluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid (Intermediate 39a). The mixed fractions were further purified by column chromatography (silica, 0-3% methanol/DCM) followed by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% formic acid) to afford 2,3-difluoro-6-(1H-1,2,3-triazol-1-yl)benzoic acid (Intermediate 39b).

Workup

  1. customPrepared
  2. customThe crude solid was purified by column chromatography (silica, 0-3% methanol/DCM)

Sources & evidence

ORD record
ord-24b6f449ebf14855917ce83833a19630
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

Loading…