3-Acetylbenzonitrile → 3-Isopropenylbenzonitrile

HRID 1784944

Reaction equation

HRID 1784944 reaction equation
[Li][CH2:2]CCC.[C:6]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])(=O)[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:7]=[C:6]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])[CH3:2]

Participants

5

Reactant 2

HCID 802223-AcetylbenzonitrileHCID 178418339Butyllithium

Product 1

HCID 121802503-IsopropenylbenzonitrileYield 86%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To the methyl triphenylphosphoniumbromide (4.3 grn, 12 mmol) in THF at 0° C., n-BuLi (1.6M, 7.5 ml, 12 mmol) was added and stirred for 30 min. Then 3-acetylbenzonitrile in THF was slowly added and the reaction mixture was stirred at 0° C. for further 3 h. Then reaction mixture was quenched with aqeous ammonium chloride and diluted with ethyl acetate. Organic layer was washed with water, brine and dried. Crude residue after column purification yielded 3-(prop-1-en-2-yl)benzonitrile in 86% yield.

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for further 3 h
  2. customThen reaction mixture
  3. customwas quenched with aqeous ammonium chloride
  4. additiondiluted with ethyl acetate
  5. washOrganic layer was washed with water, brine
  6. customdried
  7. customCrude residue after column purification

Sources & evidence

ORD record
ord-e1d1ebcc11454a64b93acbc82c01bed0
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Linked notes

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