2-Bromopyridine → 2-(Tributylstannyl)pyridine

HRID 415142Notes

Reaction equation

HRID 415142 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[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].[Cl-].[NH4+]>C1COCC1.CCCCCC>[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

7

Reactant 4

HCID 79732-BromopyridineHCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 6077842-(Tributylstannyl)pyridineYield 35%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

2-bromopyridine (14.9 g, 93.1 mmol) in anhydrous THF (700 mL) was cooled to −78° C. under a stream of nitrogen gas, n-BuLi in hexane (54 mL) were added thereto and the mixture was stirred for 30 min. Tributyltin chloride (29 mL, 108 mmol) was added and the mixture was stirred, at −78° C. for 2 hours and afterwards at −20° C. for 3 hours. It was poured into an aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried and the solvent was evaporated. The residue was purified by chromatography (petroleum ether/ethyl acetate=9/1) to give 2-(tributylstannyl)pyridine (12 g, yield 34%) as a yellow liquid, LC-MS (ESI) m/z: 370 (M+1)+.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred, at −78° C. for 2 hours and afterwards at −20° C. for 3 hours
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was dried
  5. customthe solvent was evaporated
  6. customThe residue was purified by chromatography (petroleum ether/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-cd06654dcf9a4845acbb96172e73f85a
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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