3-Bromobenzonitrile → 3-(Prop-2-en-1-yl)benzonitrile

HRID 2173215Notes

Reaction equation

HRID 2173215 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH2:10]([Sn](CCCC)(CCCC)CC=C)[CH2:11][CH2:12]C.[Li+].[Cl-]>C1(C)C=CC=CC=1.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>[CH2:12]([C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6])[CH:11]=[CH2:10]

Participants

6

Reactant 3

HCID 233813-BromobenzonitrileHCID 90628AllyltributylstannaneHCID 433294Lithium Chloride

Product 1

HCID 197666543-(Prop-2-en-1-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To solution of compound 3-bromobenzonitrile (5 g, 27 mmol) and tributyl(prop-2-en-1-yl)stannane (13.5 g, 41.2 mmol) in toluene was added Pd(PPh3)4 (300 mg) and LiCl (2.3 g, 54 mmol) under N2, and then the mixture was stirred at reflux for 18 h. The reaction mixture was quenched by the addition of water. Extracted the mixture with EtOAc and the organic layer was dried and concentrated. The residue was purified by a flash column chromatography to afford 3-(prop-2-en-1-yl)benzonitrile. 1H-NMR (300 MHz, CDCl3) δ 7.32˜7.82 (m, 4H), 5.85˜6.00 (m, 1H), 5.05˜5.17 (m, 2H), 3.42 (d, J=6.8 Hz, 2H).

Workup

  1. temperatureat reflux for 18 h
  2. customThe reaction mixture was quenched by the addition of water
  3. extractionExtracted the mixture with EtOAc
  4. customthe organic layer was dried
  5. concentrationconcentrated
  6. customThe residue was purified by a flash column chromatography

Sources & evidence

ORD record
ord-a8fae0b39f59443ea2e363a85d1c2ed8
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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