Sodium Carbonate → 4'-Cyano-2'-methylbiphenyl-4-carboxylic acid

HRID 1741040Notes

Reaction equation

HRID 1741040 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].B([C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)=[C:3]([CH3:10])[CH:4]=1)#[N:7]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 27374944-Bromo-3-methylbenzonitrile

Product 1

HCID 218337684'-Cyano-2'-methylbiphenyl-4-carboxylic acidYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-bromo-3-methylbenzonitrile (5 g, 0.026 mol) was suspended in 1,2-dimethoxyethane (100 ml) and treated with 4-boronobenzoic acid (2.4 g, 0.026 mol) followed by a solution of sodium carbonate (11.65 g, 0.11 mmol) in water (100 ml). The mixture was flushed with argon and tetrakis(triphenylphosphine)palladium (0) (0.55 g) was added. The reaction mixture was then heated to reflux with stirring. After 24 h, the 1,2-dimethoxyethane was removed by evaporation under reduced pressure and the aqueous residue was washed with ethyl acetate. The aqueous layer was then acidified to pH 1 and the resultant solid was filtered off and was dried in vacuo to give the title compound as a white solid (4.16 g, 69%).

Workup

  1. customThe mixture was flushed with argon and tetrakis(triphenylphosphine)palladium (0) (0.55 g)
  2. additionwas added
  3. temperatureThe reaction mixture was then heated
  4. temperatureto reflux
  5. customthe 1,2-dimethoxyethane was removed by evaporation under reduced pressure
  6. washthe aqueous residue was washed with ethyl acetate
  7. filtrationthe resultant solid was filtered off
  8. customwas dried in vacuo

Sources & evidence

ORD record
ord-0b72d8d6757e473f8c3347ce1c2681a4
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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