Cesium carbonate → Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

HRID 1845263Notes

Reaction equation

HRID 1845263 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6](Br)[CH:5]=1.B(O)(O)[C:14]1[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.O.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>[OH:10][C:8]1[CH:9]=[C:4]([C:3]([O:2][CH3:1])=[O:12])[CH:5]=[C:6]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 79799Tolylboronic acidHCID 53216607Methyl 3-bromo-5-hydroxybenzoate

Product 1

HCID 58187967Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a stirred solution of 3-bromo-5-hydroxy-benzoic acid methyl ester (4.09 g, 17.7 mmol) and p-tolylboronic acid (2.86 g, 21 mmol) in toluene (36 mL) was added cesium carbonate (7.14 g, 22 mmol) in water (3.6 mL) at room temperature. The mixture was purged with nitrogen, and tetrakis(triphenylphosphine)palladium(0) (1.05 g, 0.906 mmol) was added. The reaction mixture was subjected to microwave irradiation at 110° C. for 1 hour. After cooling, the mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by flash chromatography to afford the title compound.

Workup

  1. additionwas added
  2. customirradiation at 110° C. for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-28ceccff6b804415acd3a680ee7674ba
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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