Hydrochloric Acid → 4-(methylsulfonyl)-Biphenyl-2-carboxylic acid

HRID 2117459Notes

Reaction equation

HRID 2117459 reaction equation
I[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[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+].Cl>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:14][S:11]([C:8]1[CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)(=[O:13])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 574452812-Iodo-5-methanesulfonyl-benzoic acid

Product 1

HCID 574452544-(methylsulfonyl)-Biphenyl-2-carboxylic acidYield 93.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

A mixture of 15 mmol 2-iodo-5-methanesulfonyl-benzoic acid, 31 mmol phenylboronic acid, 45 mmol sodium carbonate and 34 mg palladium(II)-acetate in 100 ml water is stirred at room temperature for 60 hours. The reaction mixture is acidified by careful addition of concentrated hydrochloric acid and extracted 3 times with ethyl acetate. The organic phase is dried, concentrated and the residue crystallized from diethyl ether to yield the title compound (3.87 g, 91%) as a slightlyyellow solid, MS (m/e): 275.0 (M−H+, 100%).

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. customThe organic phase is dried
  3. concentrationconcentrated
  4. customthe residue crystallized from diethyl ether

Sources & evidence

ORD record
ord-505634e974e44c6b859851dbabeebe38
Source dataset
uspto-grants-2008_10
Patent number
US07442710B2

Reaction notes

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