Tributylvinyltin → HCID 66917982, compound

HRID 2080560Notes

Reaction equation

HRID 2080560 reaction equation
[Cl:1][C:2]1[C:3](F)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH2:10]([Sn](CCCC)(CCCC)C=C)[CH2:11]CC>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:1][C:2]1[C:3]([CH:10]=[CH2:11])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 27832563,5-Dichloro-2-fluoropyridine

Product 1

HCID 66917982HCID 66917982, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

20.06 g of 3,5-dichloro-2-fluoropyridine (0.110 mol), 30.46 ml of tributyl-vinyl-stannane (0.103 mol), 6.00 g (0.00518 mol) of Pd(PPh3)4 are refluxed in 400 ml of toluene for five hours. The reaction mixture is washed thrice with a saturated aqueous solution of potassium fluoride 200 ml), once with water (300 ml), once with brine (300 ml). The combined aqueous phases are extracted with 100 ml of toluene. After separation, the combined organic phases are dried over magnesium sulfate, filtered, concentrated to dryness and purified on silica to yield to 15.05 g of 3,5-dichloro-2-vinylpyridine (62%) with 75% purity.

Workup

  1. washThe reaction mixture is washed thrice with a saturated aqueous solution of potassium fluoride 200 ml), once with water (300 ml)
  2. extractionThe combined aqueous phases are extracted with 100 ml of toluene
  3. customAfter separation
  4. dry with materialthe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. custompurified on silica

Sources & evidence

ORD record
ord-646022fb6a284f17b246b6626459e0b4
Source dataset
uspto-grants-2011_04
Patent number
US07932396B2

Reaction notes

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