Ethyl Bromide → 2-Ethoxybenzonitrile

HRID 1016346Notes

Reaction equation

HRID 1016346 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[CH3:17]>CC(C)=O>[CH2:16]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH3:17]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 119072-Hydroxybenzonitrile

Product 1

HCID 5769222-Ethoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

25 g (210 mmol) of 2-hydroxybenzonitrile, 87 g of potassium carbonate and 34.3 g (314.8 mmol) of ethyl bromide in 500 ml of acetone are refluxed overnight. The solid is filtered off, the solvent is removed under reduced pressure and the residue is distilled under reduced pressure. This gives 30.0 g (97%) of a colourless liquid.

Workup

  1. filtrationThe solid is filtered off
  2. customthe solvent is removed under reduced pressure
  3. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-41ed53f940c64a7c887c7981f9199408
Source dataset
uspto-grants-2002_11
Patent number
US06476029B1

Reaction notes

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