Water → 4-(3-Chloropyridin-2-yl)benzoic acid

HRID 1497479Notes

Reaction equation

HRID 1497479 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.O.C([O-])([O-])=O.[Na+].[Na+].B(O)(O)[C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][CH:18]=1>COCCOC.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>[Cl:8][C:7]1[C:2]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][CH:18]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 169882,3-DichloropyridineHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 221704544-(3-Chloropyridin-2-yl)benzoic acidYield 75.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 5.3 g (36.1 mmol) 2,3-dichloropyridine in 200 mL 1,2-dimethoxyethane and 200 mL distilled water were added 22.3 g (0.21 mol) Na2CO3, 5.0 g (30.1 mmol) 4-carboxylphenylboronic acid and 0.5 g Pd(PPh3)4, followed by mixing for 18 hours under a heat flux condition by stirring. After being cooled to room temperature, the solution was 50% concentrated in a vacuum. The aqueous layer was washed with ethyl acetate and adjusted into pH 1 with conc. HCl. Thereafter, extraction with ethyl acetate was conducted three times and the organic layer was dried over magnesium sulfate and concentrated in a vacuum. The concentrate was separated using column chromatography (developing solvent: chloroform/methanol=10/1) to afford 5.3 g of 4-(3-chloropyridin-2-yl)benzoic acid as a white precipitate (yield: 75%).

Workup

  1. additionby mixing for 18 hours under a heat flux condition
  2. concentrationconcentrated in a vacuum
  3. washThe aqueous layer was washed with ethyl acetate
  4. extractionThereafter, extraction with ethyl acetate
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated in a vacuum
  7. customThe concentrate was separated

Sources & evidence

ORD record
ord-22cf5fc7b8c144099a20a414eb20a226
Source dataset
uspto-grants-2015_12
Patent number
US09199965B2

Reaction notes

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