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

HRID 2177508Notes

Reaction equation

HRID 2177508 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 300 mg (0.949 mmol) 2-iodo-4-trifluoromethyl-benzoic acid (CAS: 54507-44-7), 239 mg (1.898 mmol) phenylboronic acid, 302 mg (2.847 mmol) sodium carbonate and 10.7 mg (0.0475 mmol) palladium acetate in 4.5 ml water was stirred at room temperature for 48 hours. The mixture was filtered and the filtrate was acidified with 37% HCl. The mixture was stirred at room temperature for 30 minutes. The solid was filtered, washed with water and dried 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

Sources & evidence

ORD record
ord-fb3428a79e8a4effb34dc3775a7612cf
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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