Water → 4'-Methoxy-3-methyl[1,1'-biphenyl]-4-carboxylic acid

HRID 1354027Notes

Reaction equation

HRID 1354027 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.C(O)C>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 995704-Bromo-2-methylbenzoic acidHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 136359884'-Methoxy-3-methyl[1,1'-biphenyl]-4-carboxylic acidYield 89.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

4-Bromo-2-methyl-benzoic acid (2.15 g, 10 mmol), 4-methoxy-phenylboronic acid (1.52 g, 10 mmol) and sodium carbonate (3.24 g, 30 mmol) in a mixture of toluene, water and ethanol (15 mL:6 mL:3 mL) was sparged with nitrogen for 5 minutes. To this was added palladium acetate (0.014 g). The mixture was heated at reflux, under a static pressure of nitrogen, for 24 hours. The sample was diluted with water and ethyl acetate (50 mL each) and the pH was adjusted to 1. The layers were separated and the aqueous phase was extracted with ethyl acetate. The organic extracts were combined and washed with water and brine. The sample was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The resulting solid was recrystallized from ethyl acetate/hexanes to yield the title compound (2.16 g ) as a white solid, m.p 199–201° C.

Workup

  1. customwas sparged with nitrogen for 5 minutes
  2. additionTo this was added palladium acetate (0.014 g)
  3. temperatureThe mixture was heated
  4. temperatureat reflux, under a static pressure of nitrogen, for 24 hours
  5. additionThe sample was diluted with water and ethyl acetate (50 mL each)
  6. customThe layers were separated
  7. extractionthe aqueous phase was extracted with ethyl acetate
  8. washwashed with water and brine
  9. dry with materialThe sample was dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe resulting solid was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3aea23f36ffc4c0c8a62e038bef87614
Source dataset
uspto-grants-2007_05
Patent number
US07223752B2

Reaction notes

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