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

HRID 1950925Notes

Reaction equation

HRID 1950925 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 HCl 37%. 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-9268d321e0ee49bdada1fb2f69f9a2d1
Source dataset
uspto-grants-2013_03
Patent number
US08404673B2

Reaction notes

Loading…