Sodium Carbonate → 4′-(1H-1,2,4-Triazol-1-yl)[1,1′-biphenyl]-4-carboxylic acid

HRID 2392673Notes

Reaction equation

HRID 2392673 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[C:13](=[O:16])([O-])[O-:14].[Na+].[Na+]>COCCOC.O>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:6]3[CH:11]=[CH:10][C:9]([C:13]([OH:14])=[O:16])=[CH:8][CH:7]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 18980104HCID 18980104, compound

Product 1

HCID 189801154′-(1H-1,2,4-Triazol-1-yl)[1,1′-biphenyl]-4-carboxylic acidYield 184.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-(1,2,4-Triazol-1-yl)bromobenzene (340 mg, 1.5 mmol), 4-carboxylic acid benzene boronic acid (250 mg, 1.5 mmol), sodium carbonate (650 mg, 4 eq), tetrakis (triphenylphosphine)palladium(0) (50 mg) in DME (25 ml) and water (25 ml) was heated under argon at reflux for 24 h, cooled, evaporated to dryness under reduced pressure, partitioned between saturated aqueous sodium carbonate solution (50 ml) and ethyl acetate (50 ml), the aqueous extracts acidified with conc. HCl and dried in vacuo to afford the title compound as a pale yellow crystalline solid (367 mg, 92%).

Workup

  1. temperatureat reflux for 24 h
  2. temperaturecooled
  3. customevaporated to dryness under reduced pressure
  4. custompartitioned between saturated aqueous sodium carbonate solution (50 ml) and ethyl acetate (50 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-680ddc3f3f3d46cba52b2f02e6895a68
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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