Ethyl Acetate → 4-(Pyridin-4-yl)benzoic acid hydrochloride

HRID 2104376Notes

Reaction equation

HRID 2104376 reaction equation
[ClH:1].Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[C:9]([C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)([OH:11])=[O:10].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.O.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>[ClH:1].[N:6]1[CH:7]=[CH:8][C:3]([C:15]2[CH:16]=[CH:17][C:12]([C:9]([OH:11])=[O:10])=[CH:13][CH:14]=2)=[CH:4][CH:5]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 574326074-(Pyridin-4-yl)benzoic acid hydrochlorideYield 59%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

4-Bromopyridine hydrochloride (11.7 g) and 4-carboxyphenylboronic acid (10.0 g) were dissolved in a solvent mixture of toluene (250 mL) and water (250 mL), and to the solution were sequentially added tetrakis(triphenylphosphine)palladium(0) (5.0 g) and anhydrous sodium carbonate (25.4 g), followed by heating under reflux at 120° C. for 19 hours. After the resultant mixture was cooled to room temperature, ethyl acetate was added thereto, and the thus-obtained mixture was extracted with water. Concentrated HCl was added to the aqueous layer, to thereby make the mixture acidic. The aqueous layer was washed with ethyl acetate, and was concentrated. The resultant solid was collected by filtration, to thereby give the title compound (8.37 g).

Workup

  1. temperatureby heating
  2. extractionthe thus-obtained mixture was extracted with water
  3. additionConcentrated HCl was added to the aqueous layer
  4. washThe aqueous layer was washed with ethyl acetate
  5. concentrationwas concentrated
  6. filtrationThe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-8d97e1d8083843dabfc1c7464ddebb2c
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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