Allyltributylstannane → 4-Allyl-2,6-difluorobenzonitrile

HRID 1519587Notes

Reaction equation

HRID 1519587 reaction equation
Br[C:2]1[CH:9]=[C:8]([F:10])[C:5]([C:6]#[N:7])=[C:4]([F:11])[CH:3]=1.[CH2:12]([Sn](CCCC)(CCCC)CCCC)[CH:13]=[CH2:14].[Li+].[Cl-]>C1(C)C=CC=CC=1>[CH2:14]([C:2]1[CH:9]=[C:8]([F:10])[C:5]([C:6]#[N:7])=[C:4]([F:11])[CH:3]=1)[CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 27569164-Bromo-2,6-difluorobenzonitrile

Product 1

HCID 675131164-Allyl-2,6-difluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-bromo-2,6-difluorobenzonitrile (2.0 g, 9.2 mmol), allyl-tributyl-stannane (3.65 g, 11.0 mmol), LiCl (1.17 mg, 28 mmol) and Pd(PPh)4 (0.2 g) in 70 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-2,6-difluorobenzonitrile. MS m/z: 180 (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-87bf74a2e85841e0b4e637fe9ee412a6
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

Loading…