Allyltributylstannane → 4-Allyl-3-methoxybenzonitrile

HRID 1519593Notes

Reaction equation

HRID 1519593 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11].[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]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11])[CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 225911814-Bromo-3-methoxybenzonitrile

Product 1

HCID 675133484-Allyl-3-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-bromo-3-methoxybenzonitrile (1.4 g, 6.7 mmol), allyl-tributyl-stannane (2.7 g, 8.1 mmol), LiCl (0.86 mg, 20 mmol) and Pd(PPh)4 (0.2 g) in 25 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-3-methoxybenzonitrile. MS m/z: 174 (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-471152da6fcf4871bc1fe388b8187691
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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