2-Bromopyridine → Pyridine, 2-(trimethylstannyl)-

HRID 263836Notes

Reaction equation

HRID 263836 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[CH3:13][Sn:14](Cl)([CH3:16])[CH3:15].C1COCC1>CCOCC>[CH3:13][Sn:14]([CH3:16])([CH3:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 79732-BromopyridineHCID 8028TetrahydrofuranHCID 14016Trimethyltin chlorideHCID 178418339Butyllithium

Product 1

HCID 11021057Pyridine, 2-(trimethylstannyl)-Yield 51%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 15.7 mL of 1.6M n-butyllithium (25.1 mmol) in anhydrous ether (25 mL) was stirred under Ar at -78° C. and to this was added a solution of 2-bromopyridine (3.97 g, 25.1 mmol) in anhydrous ether (12.5 mL). The resulting orange solution was stirred for 2 h, and trimethyltin chloride in THF (26.0 mmol, 26 and, 1.0M) added over 30 min. The reaction was stirred for 1 h at -78° C. then warmed to room temperature over 1 h, filtered and the filtrate evaporated. Distillation afforded 3.1 g (51%) of the title compound as a colorless liquid which solidified in the receiver flask. B.p. 65° C./2 mm Hg; Literature B.p. 75° C./4 mm Hg.

Workup

  1. stirringThe reaction was stirred for 1 h at -78° C.
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. distillationDistillation

Sources & evidence

ORD record
ord-d2b6ccbd3cb44b6595c8500e40e2a855
Source dataset
uspto-grants-1997_07
Patent number
US05645985

Reaction notes

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