4-Iodobenzonitrile → 4-allyl-benzonitrile

HRID 269988Notes

Reaction equation

HRID 269988 reaction equation
[CH2:1]([Sn](CCCC)(CCCC)CCCC)[CH:2]=[CH2:3].I[C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.[F-].[K+]>O1CCOCC1.C(OCC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH2:3]([C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1)[CH:2]=[CH2:1]

Participants

8

Reactant 3

HCID 764674-IodobenzonitrileHCID 90628AllyltributylstannaneHCID 522689Potassium Fluoride

Product 1

HCID 98555034-allyl-benzonitrileYield 70.9%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Add allyl tri-n-butylstannane (39.3 mmol, 12.18 ml) dropwise to a stirred solution of 4-iodo-benzonitrile (6 g, 26.2 mmol), tetrakis(triphenylphosphine)palladium(0) (1.31 g, 1.5 mmol) and copper (I) iodide (399 mg, 2.09 mmol) in 30 ml of dry 1,4-dioxane under argon atmosphere. Reflux the mixture for 24 hours and then cool to room temperature. Dilute with 40 ml of diethyl ether and add 20 ml of saturated solution of KF and stir for 2 hours. Filter the mixture and wash the organic layer with water (20 ml), brine (20 ml) and dry over sodium sulfate. Evaporate in vacuo and purify by flash chromatography in silica using hexane-ethyl acetate as eluent (20:1) to afford 2.66 g (70%) of 4-allylbenzonitrile

Workup

  1. temperatureReflux the mixture for 24 hours
  2. filtrationFilter the mixture
  3. washwash the organic layer with water (20 ml), brine (20 ml)
  4. dry with materialdry over sodium sulfate
  5. customEvaporate in vacuo
  6. custompurify by flash chromatography in silica

Sources & evidence

ORD record
ord-cc4b364b390c4bc9bf319b38fc9c6a3a
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Reaction notes

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