Allyltributylstannane → 3-(4-Cyano-3-fluorophenyl)-1-propene

HRID 1519597Notes

Reaction equation

HRID 1519597 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.[CH2:11]([Sn](CCCC)(CCCC)CCCC)[CH:12]=[CH2:13].[Li+].[Cl-]>C1(C)C=CC=CC=1>[CH2:13]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1)[CH:12]=[CH2:11]

Participants

5

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 7360294-Bromo-2-fluorobenzonitrile

Product 1

HCID 247217663-(4-Cyano-3-fluorophenyl)-1-propene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-bromo-2-fluorobenzonitrile (250 mg, 1.3 mmol), allyl-tributyl-stannane (500 mg, 1.5 mmol), LiCl (160 mg, 3.8 mmol) and Pd(PPh)4 (15 mg) in 5 mL of anhydrous toluene was refluxed under N2 overnight. Checked the reaction with TLC and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the product 4-allyl-2-fluorobenzonitrile. MS m/z: 162 (M+1)+.

Workup

  1. temperaturewas refluxed under N2 overnight
  2. customChecked the reaction with TLC
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4af7eba7957544a3beb4b98cb607ea01
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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