Toluene → Methyl 4'-methyl-5-(methylsulfonyl)biphenyl-3-carboxylate

HRID 1845157Notes

Reaction equation

HRID 1845157 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].B(O)(O)[C:17]1[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([C:2]2[CH:11]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=2)=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 79799Tolylboronic acidHCID 22101072Methyl 3-bromo-5-methanesulfonylbenzoate

Product 1

HCID 58188120Methyl 4'-methyl-5-(methylsulfonyl)biphenyl-3-carboxylate

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

To a mixture of methyl 3-bromo-5-(methylsulfonyl)benzoate (0.65 g, 2.2 mmol), p-tolylboronic acid (0.332 g, 2.44 mmol), toluene (10 mL), cesium carbonate (0.795 g, 2.44 mmol), and water (1 mL) under argon was added tetrakis(triphenylphosphine)-palladium(0) (128 mg, 0.111 mmol). The mixture was heated under reflux for 15 h. After cooling, the mixture was filtered through Celite and the filter cake was washed with EtOAc. The filtrate was washed with brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel column (0-100% EtOAc/hexane) to yield a white solid. LC-MS: 3.26 min, 305.3 [M+1]+ (weak).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 15 h
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite
  5. washthe filter cake was washed with EtOAc
  6. washThe filtrate was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column (0-100% EtOAc/hexane)
  10. customto yield a white solid
  11. custom3.26 min, 305.3 [M+1]+ (weak)

Sources & evidence

ORD record
ord-b3bd2fad637547ebb8acb0c6359d4722
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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