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

HRID 2404296Notes

Reaction equation

HRID 2404296 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+].O>C1(C)C=CC=CC=1.CCOC(C)=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

8

Reactant 4

HCID 962WaterHCID 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 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-bromo-3-(trifluoromethyl)benzoate (6.0 g, 21.2 mmol), o-tolylboronic acid (3.17 g, 23.3 mmol), potassium carbonate (14.7 g, 106.0 mmol), tetrakis(triphenylphosphine)palladium(0) (2.45 g, 2.12 mmol) were taken up in toluene (30 mL) and water (30 mL) under N2 atmosphere. The reaction mixture was refluxed for 3 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and rinsed with toluene (200 mL). The filtrate was concentrated to afford a brown oil which was taken up in EtOAc (200 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 (50 mL), water (50 mL) and brine (50 mL), dried over MgSO4 and concentrated affording the title compound as a brown oil (6.4 g, quantitative). HPLC (Method A) Rt 5.33 min (Purity: 60%).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. filtrationfiltered over a pad of celite
  3. washrinsed with toluene (200 mL)
  4. concentrationThe filtrate was concentrated
  5. customto afford a brown oil which
  6. washThe organic layer was washed with a saturated aqueous solution of NaHCO3 (50 mL), water (50 mL) and brine (50 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-06f5a378489a4eb3bb293453968dd775
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

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