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

HRID 415284Notes

Reaction equation

HRID 415284 reaction equation
B([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(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:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 142684-BromopyridineHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 15208114-(Pyridin-4-yl)benzoic acidYield 90.4%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-boronobenzoic acid (1.66 g, 10 mmol) and 4-bromopyridine (1.72 g, 11 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 degassed and purged withed nitrogen. The mixture was stirred at 100° C. for 24 h. 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 1.8 g of white solid of 4-(pyridin-4-yl)benzoic acid. Yield: 90%. LC-MS (ESI) m/z: 200 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-fa2e3dfe7e6149e49acc012971419db3
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

Loading…