2-Bromopyridine → 2-(Tributylstannyl)pyridine

HRID 1956325Notes

Reaction equation

HRID 1956325 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 (Na2 SO4) 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. customThe organic layer is dried (Na2 SO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-0198a7f355f64c08b9b939f3412b1452
Source dataset
uspto-grants-1998_07
Patent number
US05780471

Reaction notes

Loading…