Potassium Carbonate → Methyl 2'-methyl-2-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

HRID 1630974Notes

Reaction equation

HRID 1630974 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[C:16]1([CH3:25])[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>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>[CH3:25][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 10891333Methyl 4-bromo-3-(trifluoromethyl)benzoate

Product 1

HCID 58554190Methyl 2'-methyl-2-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylateYield 102.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A degassed mixture of methyl 4-bromo-3-(trifluoromethyl)benzoate (6.00 g, 21.2 mmol), o-tolylboronic acid (3.17 g, 23.3 mmol), potassium carbonate (14.65 g, 106 mmol), Pd(PPh3)4 (2.45 g, 2.12 mmol) was prepared in toluene (30 mL) and water (30 mL), and then heated at reflux for 3 hours. The reaction mixture was filtered through a pad of Celite and diluted with EtOAc (200 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 (50 mL), water (50 mL) and brine (50 mL), and then dried (MgSO4). The solvents were removed under reduced pressure affording the title compound as a brown oil (6.4 g, quantitative) used without further purification in the next step. HPLC (Method A), Rt 5.3 min (Purity: 60.0%).

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. additiondiluted with EtOAc (200 mL)
  4. washThe organic layer was washed with a saturated aqueous solution of NaHCO3 (50 mL), water (50 mL) and brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-f5fbcf0b80b5429485feb082bc7a6944
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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