Hydrochloric Acid → 3-Fluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acid

HRID 1524910Notes

Reaction equation

HRID 1524910 reaction equation
[F:1][C:2]1[C:3]([N:10]2[N:14]=[CH:13][CH:12]=[N:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#N.[OH-:15].[Na+].Cl.C[OH:19]>>[F:1][C:2]1[C:3]([N:10]2[N:14]=[CH:13][CH:12]=[N:11]2)=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]([OH:19])=[O:15]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 670864473-fluoro-2-(2H-1,2,3-triazol-2-yl)benzonitrile

Product 1

HCID 670865493-Fluoro-2-(2H-1,2,3-triazol-2-yl)benzoic acidYield 18%

Procedure

To 3-fluoro-2-(2H-1,2,3-triazol-2-yl)benzonitrile (1.5 g, 8.0 mmol) in MeOH (30 mL) was added 2M aq. NaOH (10 mL). The reaction was heated at reflux for 15 h, then cooled to rt, acidified with 1N aq. HCl to pH=1 and extracted with DCM (2×). The combined organics were washed with brine and dried (Na2SO4). Purification via Agilent (Reverse-Phase HPLC, basic conditions) gave the title compound (290 mg, 18%). 1H NMR (CDCl3): 7.90 (s, 2H), 7.89-7.85 (m, 1H), 7.63-7.56 (m, 1H), 7.50-7.44 (m, 1H) and 3-methoxy-2-(2H-1,2,3-triazol-2-yl)benzoic acid (Intermediate 53, 140 mg, 8%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 15 h
  3. extractionextracted with DCM (2×)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customPurification via Agilent (Reverse-Phase HPLC, basic conditions)

Sources & evidence

ORD record
ord-5a3d7419ca334b0c97af6de5895cc0e5
Source dataset
uspto-grants-2015_07
Patent number
US09079911B2

Reaction notes

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