Allyl bromide → 4-[2-(2-Propenyloxy)acetyl]benzonitrile

HRID 2427142Notes

Reaction equation

HRID 2427142 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=[O:4].S([O-])([O-])(=O)=O.[Ca+2].[CH2:19](Br)[CH:20]=[CH2:21]>CCOC(C)=O.[Ag]=O>[CH2:21]([O:1][CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=[O:4])[CH:20]=[CH2:19]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 24497Calcium SulfateHCID 179928864-(2-Hydroxyacetyl)benzonitrile

Product 1

HCID 620298594-[2-(2-Propenyloxy)acetyl]benzonitrile

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.7 g of 4-(2-hydroxyacetyl)benzonitrile in allyl bromide (15 mL) is added 10.2 g calcium sulfate and 6.7 g of silver oxide. The mixture is stirred under argon and in the dark for 2 hours. The mixture is diluted with AcOEt, filtered on celite, concentrated and purified on silica gel (ethyl acetate/cyclohexane: 0/100 to 50/50) to give the desired compound.

Workup

  1. filtrationfiltered on celite
  2. concentrationconcentrated
  3. custompurified on silica gel (ethyl acetate/cyclohexane: 0/100 to 50/50)

Sources & evidence

ORD record
ord-9f71bd9a2dac498ca4cbdc8ecc20e832
Source dataset
uspto-grants-2011_06
Patent number
US07968581B2

Reaction notes

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