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

HRID 2175012Notes

Reaction equation

HRID 2175012 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 1 N aq. HCl to pH 1 and extracted with CH2Cl2 (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 CH2Cl2 (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-82b09f9970f14c1a8f16e7a9e72376fd
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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