Tributylvinyltin → 2-Fluoro-4-vinylbenzonitrile

HRID 1990752Notes

Reaction equation

HRID 1990752 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-22bbbb60448f4922ae166f7ee18c5380
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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