Toluene → Methyl 2-methoxy-2'-methylbiphenyl-4-carboxylate

HRID 2244193Notes

Reaction equation

HRID 2244193 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[O:19][CH3:20].C1(C)C=CC=CC=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[CH3:16][O:15][C:13]([C:12]1[CH:17]=[CH:18][C:9]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH3:7])=[C:10]([O:19][CH3:20])[CH:11]=1)=[O:14]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 14570117Methyl 4-bromo-3-methoxybenzoate

Product 1

HCID 53941402Methyl 2-methoxy-2'-methylbiphenyl-4-carboxylateYield 99%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

A solution consisting of toluene (100 mL), ethanol (50 mL), and water (50 mL), was sparged with dry nitrogen gas for 45 minutes. To the solvent mixture was added 4-bromo-3-methoxybenzoic acid methyl ester of Step B (26.5 mmol), o-tolylboronic acid (29.1 mmol), and sodium carbonate (112.5 mmol). The mixture was sparged with nitrogen gas for an additional ten minutes. Tetrakis(triphenylphosphine)palladium(0) (1 mmol) was added to the mixture which was then heated at 105° C. for 6 hours. The mixture was cooled and the phases separated. The organic phase was washed three times with a sequence of saturated aqueous sodium carbonate, and brine. The organics were dried over anhydrous sodium sulfate, and evaporated to an oil. Chromatography on silica gel using dichloromethane and hexane (3:1) provided the title compound as a clear oil (6.7g, 99%).

Workup

  1. customwas sparged with dry nitrogen gas for 45 minutes
  2. customThe mixture was sparged with nitrogen gas for an additional ten minutes
  3. temperatureThe mixture was cooled
  4. customthe phases separated
  5. washThe organic phase was washed three times with a sequence of saturated aqueous sodium carbonate, and brine
  6. dry with materialThe organics were dried over anhydrous sodium sulfate
  7. customevaporated to an oil

Sources & evidence

ORD record
ord-6b55d202d84c4ae0a9c6e37fe4b8916e
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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