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

HRID 639234Notes

Reaction equation

HRID 639234 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 for 45 minutes. To the mixture was added methyl 4-bromo-3-methoxybenzoate of step B (26.5 mmol), o-tolylboronic acid (29.1 mmol), and sodium carbonate (112.5 mmol). The mixture was sparged with nitrogen for an additional ten minutes. Terakis(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 organic phase was washed three times in sequence with saturated aqueous sodium carbonate and brine. The organics were dried over anhydrous sodium sulfate, filtered, and evaporated to an oil. Flash chromatography of the residue on silica gel using dichloromethane/hexane (3:1) yielded the title compound as a clear oil (6.7 g, 99%).

Workup

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

Sources & evidence

ORD record
ord-74b5282b58404899945b3ccd7801d262
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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