Sodium Carbonate → 3',4-Difluoro-[1,1'-biphenyl]-3-carboxylic acid

HRID 1771586Notes

Reaction equation

HRID 1771586 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>O.CCO.CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:11][C:5]1[CH:4]=[CH:3][C:2]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([F:12])[CH:18]=2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 27363155-Bromo-2-fluorobenzoic acid

Product 1

HCID 463123323',4-Difluoro-[1,1'-biphenyl]-3-carboxylic acidYield 97%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 5-bromo-2-fluorobenzoic acid (3 g, 13.2 mmol, 1.0 eq) and 3-fluorophenyl boronic acid (2.1 g, 15.1 mmol, 1.1 eq) in water (15 mL), EtOH (15 mL) and DMF (60 mL) was added Na2CO3 (5.81 g, 54.8 mmol, 4.1 eq) and Pd(PPh3)4 (1.58 g, 1.37 mmol, 0.1 eq). The reaction mixture was heated at 100° C. under nitrogen for 4 h, then cooled to room temperature. The resulting mixture was poured into water and extracted with ethyl acetate. The organic extracts were combined, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a white powder (3 g, 97%).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4dd1889d74ea40199768310501908119
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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