Tributylvinyltin → 2-Fluoro-4-vinylbenzonitrile

HRID 1246668Notes

Reaction equation

HRID 1246668 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.[CH:11]([Sn](CCCC)(CCCC)CCCC)=[CH2:12]>C1(C)C=CC=CC=1>[F:10][C:4]1[CH:3]=[C:2]([CH:11]=[CH2:12])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 7360294-Bromo-2-fluorobenzonitrile

Product 1

HCID 219046072-Fluoro-4-vinylbenzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-bromo-2-fluorobenzonitrile (4.92 g, 0.0246 mol), vinyltributyltin (0.78 g, 0.246 mol), and tetrakistriphenylphosphine (0.67 g, 0.58 mmol) in 250 mL of toluene was refluxed under nitrogen overnight. The solvent was evaporated and the residue was flash chromatographed on silica gel with heptane:CH2Cl2 (1:1) to pure CH2Cl2. A colourless oil was obtained that crystallised. Yield: 3.0 g (82%).

Workup

  1. customThe solvent was evaporated
  2. customchromatographed on silica gel with heptane:CH2Cl2 (1:1) to pure CH2Cl2
  3. customA colourless oil was obtained
  4. customthat crystallised

Sources & evidence

ORD record
ord-cd9f1aea16614f398b75f57b875aba62
Source dataset
uspto-grants-2006_10
Patent number
US07129233B2

Reaction notes

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