Sodium Carbonate → 5-(Trifluoromethyl)biphenyl-2-carboxylic acid

HRID 659213Notes

Reaction equation

HRID 659213 reaction equation
I[C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:12][C:11]([F:14])([F:13])[C:9]1[CH:10]=[C:2]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:3]([C:4]([OH:6])=[O:5])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 162440902-Iodo-4-(trifluoromethyl)benzoic acid

Product 1

HCID 463151975-(Trifluoromethyl)biphenyl-2-carboxylic acidYield 89.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-iodo-4-trifluoromethyl-benzoic acid (CAS: 54507-44-7) (300 mg, 0.949 mmol) phenylboronic acid (239 mg, 1.898 mmol), sodium carbonate (302 mg, 2.847 mmol) and palladium (II) acetate (10.7 mg, 0.0475 mmol) in 4.5 ml water was stirred at room temperature for 48 hours. The mixture was filtered and the filtrate was acidified with HC137%. The mixture was stirred at room temperature for 30 minutes. The solid was filtered, washed with water and dried in vacuo to provide 225 mg (89%) of the title compound as a brown solid. MS (m/e): 264.9 (M+H+).

Workup

  1. filtrationThe mixture was filtered
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0601b68757924014b649eee00a95772f
Source dataset
uspto-grants-2011_12
Patent number
US08080541B2

Reaction notes

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