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

HRID 1193103Notes

Reaction equation

HRID 1193103 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 64, 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-681c7c3f85244edc8e9c9e50ed035b09
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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