Ethyl Bromide → 224789-17-7

HRID 2249437Notes

Reaction equation

HRID 2249437 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-f7327fefc4104dd1a176bf4f9faef3e8
Source dataset
uspto-grants-2008_01
Patent number
US07314871B2

Reaction notes

Loading…