Allyl bromide → 5-(Allyloxy)-2-ethoxybenzonitrile

HRID 1814827Notes

Reaction equation

HRID 1814827 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:5]=1[C:6]#[N:7])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CC(C)=O>[CH2:21]([O:12][C:9]1[CH:10]=[CH:11][C:4]([O:3][CH2:1][CH3:2])=[C:5]([CH:8]=1)[C:6]#[N:7])[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 219731772-Ethoxy-5-hydroxybenzonitrile

Product 1

HCID 219731885-(Allyloxy)-2-ethoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

25 g of 2-ethoxy-5-hydroxybenzonitrile (153.2 mmol) (example 36A) and potassium carbonate (63.52 g, 459.6 mmol) are initially charged in 750 ml of acetone. 19.9 ml of allyl bromide (229.8 mmol) are added, and the mixture is stirred under reflux overnight. The mixture is filtered off and concentrated giving a mobile orange oil.

Workup

  1. temperatureunder reflux overnight
  2. filtrationThe mixture is filtered off
  3. concentrationconcentrated
  4. customgiving a mobile orange oil

Sources & evidence

ORD record
ord-4ebb451c2deb46b0b5deb7c3a7096d21
Source dataset
uspto-grants-2005_04
Patent number
US06878708B2

Reaction notes

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