2-Chloropyridine → 2-Phenylpyridine

HRID 2252653Notes

Reaction equation

HRID 2252653 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]1(B(O)O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([O-])([O-])=O.[Na+].[Na+]>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>[C:8]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 79772-ChloropyridineHCID 10340Sodium CarbonateHCID 66827Phenylboronic Acid

Product 1

HCID 138872-PhenylpyridineYield 70.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Chloropyridine (10 g, 88.0 mmol), phenylboronic acid (12.9 g, 105.7 mmol), tetrakis(triphenylphosphine)palladium (0) (5.0 g, 5 mol %) and 2M Na2CO3 (50 mL) were all dissolved in ethylene glycol dimethylether (200 mL) at room temperature, under an atmosphere of nitrogen. The mixture was refluxed for 48 hours. Ethylene glycol dimethylether was evaporated in vacuo to give a red oil, which was partitioned between water (10 mL) and EtOAc (10 mL). The EtOAc layer was separated and the aqueous layer was further extracted with EtOAc (10 mL×2). The combined EtOAc layers were dried (MgSO4) and concentrated in vacuo to a red oil. Purification by flash column chromatography (iso-hexaneethyl acetate 1:5-silica) gave the title product as a colourless oil (9.6 g, 70%).

Workup

  1. temperatureThe mixture was refluxed for 48 hours
  2. customEthylene glycol dimethylether was evaporated in vacuo
  3. customto give a red oil, which
  4. customwas partitioned between water (10 mL) and EtOAc (10 mL)
  5. customThe EtOAc layer was separated
  6. extractionthe aqueous layer was further extracted with EtOAc (10 mL×2)
  7. dry with materialThe combined EtOAc layers were dried (MgSO4)
  8. concentrationconcentrated in vacuo to a red oil
  9. customPurification by flash column chromatography (iso-hexaneethyl acetate 1:5-silica)

Sources & evidence

ORD record
ord-4f27913d2bf940db90ece6f6de8b7717
Source dataset
uspto-grants-2008_01
Patent number
US07323464B2

Reaction notes

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