Water → Ethyl 2-methylbiphenyl-4-carboxylate

HRID 2264313Notes

Reaction equation

HRID 2264313 reaction equation
O.C(=O)([O-])[O-].[Na+].[Na+].[C:8]1(B(O)O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][C:19]=1[CH3:29]>C1(C)C=CC=CC=1>[CH3:29][C:19]1[CH:20]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:27]=[CH:28][C:18]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 21729626Ethyl 4-bromo-3-methylbenzoate

Product 1

HCID 23112239Ethyl 2-methylbiphenyl-4-carboxylateYield 99.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into 150 ml of water were suspended 55.9 g of sodium carbonate and 38.6 g of phenylboronic acid. Thereto was added 51.4 g of ethyl 4-bromo-3-methylbenzoate dissolved in 400 ml of toluene and then was added 4.0 g of tetrakistriphenylphosphine palladium, followed by 2 hours of reflux with heating. After the reaction solution was cooled to room temperature, filtration was conducted using celite, water was added to the filtrate and the organic layer was extracted with toluene. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by evaporation and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate) to obtain 50.4 g of ethyl 2-methylbiphenyl-4-carboxylate as a colorless oil.

Workup

  1. temperatureof reflux
  2. temperaturewith heating
  3. filtrationfiltration
  4. additionwas added to the filtrate
  5. extractionthe organic layer was extracted with toluene
  6. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed by evaporation
  8. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-0796ad3859a342eb8a26057804eed42a
Source dataset
uspto-grants-2010_12
Patent number
US07855198B2

Reaction notes

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