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

HRID 243851Notes

Reaction equation

HRID 243851 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-4292a33d35d748f093044e20cc4de070
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

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