Ethyl Bromide → 224789-17-7

HRID 413075Notes

Reaction equation

HRID 413075 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH3:20]>CC(C)=O>[CH2:19]([O:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH3:20]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 114236802-Hydroxy-4-methoxybenzonitrile

Product 1

HCID 21896905224789-17-7

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

30.0 g (201 mmol) of 2-hydroxy-4-methoxybenzonitrile are refluxed with 83.4 g of potassium carbonate (603 mmol) and 32.88 g (301 mmol) of bromoethane in 550 ml of acetone for 18 hours. After filtration, the solvent is removed under reduced pressure and the residue is purified by silica gel chromatography (cyclohexane:ethyl acetate=10:1): 35.9 g of an oil Rf=0.37 (cyclohexane:ethyl acetate=3:1)

Workup

  1. filtrationAfter filtration
  2. customthe solvent is removed under reduced pressure
  3. customthe residue is purified by silica gel chromatography (cyclohexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-25378587c55c483c9fcfd0b86c0e7eb0
Source dataset
uspto-grants-2003_05
Patent number
US06566360B1

Reaction notes

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