Triphenylphosphine → 2,3-Dichloro-5-ethenylpyridine

HRID 1430094Notes

Reaction equation

HRID 1430094 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Br[CH2:21][C:22]1[CH:23]=[C:24]([Cl:29])[C:25]([Cl:28])=[N:26][CH:27]=1>C(Cl)(Cl)Cl>[Cl:28][C:25]1[C:24]([Cl:29])=[CH:23][C:22]([CH:21]=[CH2:1])=[CH:27][N:26]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 219623285-(Bromomethyl)-2,3-dichloropyridine

Product 1

HCID 574168492,3-Dichloro-5-ethenylpyridineYield 129.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.9 g of triphenylphosphine was added to 3.6 g of compound (7) (14.9 mmol) prepared in Example 4 dissolved in 20 mL of chloroform and the mixture was reacted at 120° C. for 10 minutes by radiating with microwave radiation. And the mixture concentrated under reduced pressure to remove chloroform, and then crystallized from diethyl ether. The crystal was added to 5 mL of 40% formaldehyde, and 50% NaOH was slowly added dropwise to be a concentration of 1.7 N. After stirring for 2 hours, the resultant was extracted with ether, and concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent: chloroform/methanol=30/1) to obtain 2.5 g of 2,3-dichloro-5-vinylpyridine (yield 97%).

Workup

  1. customthe mixture was reacted at 120° C. for 10 minutes
  2. concentrationAnd the mixture concentrated under reduced pressure
  3. customto remove chloroform
  4. customcrystallized from diethyl ether
  5. additionThe crystal was added to 5 mL of 40% formaldehyde, and 50% NaOH
  6. additionwas slowly added dropwise
  7. extractionthe resultant was extracted with ether
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was separated by column chromatography (eluting solvent: chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-cbd72c98e7d141a4b71381637d9107a7
Source dataset
uspto-grants-2015_01
Patent number
US08940769B2

Reaction notes

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