Sodium Carbonate → (1,1'-Biphenyl)-3-carboxylic acid

HRID 2111967Notes

Reaction equation

HRID 2111967 reaction equation
I[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:11]1([C:3]2[CH:4]=[C:5]([CH:9]=[CH:10][CH:2]=2)[C:6]([OH:8])=[O:7])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 120854-Iodobenzoic acidHCID 66827Phenylboronic Acid

Product 1

HCID 12854(1,1'-Biphenyl)-3-carboxylic acidYield 98.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

p-Iodo-benzoic acid (4.96 g, 20 mmol), phenyl boronic acid (2.68 g, 22 mmol), Na2CO3 (6.36 g, 60 mmol) and Pd(OAc)2 (44 mg) were dissolved in 80 ml water and heated to 50° C. for 1 hour. Filtered and washed EtOAc, then acidified with 1 M HCl and extracted into EtOAc, dried with Na2SO4, evaporated and recrystallised from EtOAc and heptane to yield 3.9 g of meta-phenyl benzoic acid as a white solid. 2-(3-Biphenyl-3-yl-ureido)-4-chloro-benzoic acid was then prepared according to method E (m.p. 181-183° C.).

Workup

  1. filtrationFiltered
  2. washwashed EtOAc
  3. extractionextracted into EtOAc
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customrecrystallised from EtOAc and heptane

Sources & evidence

ORD record
ord-034780e5a0ad4a77953af3ecf0dfa428
Source dataset
uspto-grants-2009_04
Patent number
US07521480B2

Reaction notes

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