Potassium Carbonate → 3-(Pyridin-4-yl)benzoic acid

HRID 415300Notes

Reaction equation

HRID 415300 reaction equation
B([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(O)O.Br[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:17]1[CH:18]=[CH:19][C:14]([C:4]2[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=2)[C:7]([OH:9])=[O:8])=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 142684-BromopyridineHCID 27339573-Carboxyphenylboronic acid

Product 1

HCID 27955623-(Pyridin-4-yl)benzoic acidYield 83.7%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-boronobenzoic acid (1.5 g, 9 mmol) and 4-bromopyridine (1.5 g, 9.9 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.37 mmol) was added. The mixture was stirred under reflux overnight. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.5 g 3-(pyridin-4-yl)benzoic acid. Yield: 83%. LC-MS (ESI) m/z: 200 (M+1)+.

Workup

  1. temperatureunder reflux overnight
  2. filtrationThen the hot suspension was filtered
  3. concentrationconcentrated to half of the original volume
  4. washwashed with dichloromethane
  5. filtrationfiltrated
  6. washwashed with water
  7. customThe residue was dried in vacuum

Sources & evidence

ORD record
ord-22a73cdadc2e4ca79c4a536f0124f946
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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