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

HRID 11263Notes

Reaction equation

HRID 11263 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-a4f97ceaf626467dba55ac336b431903
Source dataset
uspto-grants-2006_08
Patent number
US07098207B2

Reaction notes

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