2-Bromopyridine → 2-(Tributylstannyl)pyridine

HRID 440757Notes

Reaction equation

HRID 440757 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH2:13]([Sn:17](Cl)([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16]>O1CCCC1>[CH2:22]([Sn:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 6077842-(Tributylstannyl)pyridineYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 10.0 g of 2-bromo-pyridine under nitrogen in 100 ml of tetrahydrofuran while cooling in a dry ice-acetone bath is added dropwise 47.0 ml of a 1.6M solution of butyl lithium via syringe. Stirring is continued for 1 hour. To the reaction mixture is added dropwise 24.7 g of tributyltin chloride in 30 ml of tetrahydrofuran and stirred 1 additional hour. The reaction mixture is quenched with 20 ml of water and 100 ml additional water is added. After stirring for 20 minutes the reaction mixture is extracted with chloroform (3×100 ml). The organic layer is filtered through diatomaceous earth and the filtrate washed with saturated NaHCO3 and water. The organic layer is dried (Na2SO4) and evaporated in vacuo to give 21.2 g of the desired product. MS 379.1

Workup

  1. stirringstirred 1 additional hour
  2. customThe reaction mixture is quenched with 20 ml of water and 100 ml additional water
  3. additionis added
  4. stirringAfter stirring for 20 minutes the reaction mixture
  5. extractionis extracted with chloroform (3×100 ml)
  6. filtrationThe organic layer is filtered through diatomaceous earth
  7. washthe filtrate washed with saturated NaHCO3 and water
  8. dry with materialThe organic layer is dried (Na2SO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-b2a2d47e8de741758244be0e9d5e09e0
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

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