2,3-Dichloropyridine → 3-Chloro-2-(p-tolyl)pyridine

HRID 578588Notes

Reaction equation

HRID 578588 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C[Sn](C)(C)[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1>C1(C)C=CC=CC=1.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:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 169882,3-DichloropyridineHCID 617834Stannane, trimethyl(4-methylphenyl)-

Product 1

HCID 207099363-Chloro-2-(p-tolyl)pyridineYield 82%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

66.7 g (0.451 mol) of 2,3-dichloropyridine and 115 g (0.451 mol) of trimethyl(p-tolyl)tin were dissolved in 1 L of toluene, after which 52.1 g (0.045 mol) of Pd(PPh3)4 was added, and the mixture was heated to reflux for 6˜7 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure and to the concentration residue was added 700 mL of distilled water, followed by stirring. The organic layer was separated, treated with magnesium sulfate, filtered, and concentrated under reduced pressure, yielding 3-chloro-2-para-tolylpyridine as represented below in a 82% yield.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6˜7 hours
  3. customAfter completion of the reaction
  4. concentrationthe reaction solution was concentrated under reduced pressure and to the concentration residue
  5. additionwas added 700 mL of distilled water
  6. customThe organic layer was separated
  7. additiontreated with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb0ef573ee194e2ab1532bec1993fc25
Source dataset
uspto-grants-2015_05
Patent number
US09040572B2

Reaction notes

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