Hydrochloric Acid → 1-bromo-4-(1-ethoxyethoxy)benzene

HRID 896952Notes

Reaction equation

HRID 896952 reaction equation
[C:1]([O:4][CH2:5][CH3:6])(=[O:3])[CH3:2].[CH:7]1[C:12](O)=[CH:11][CH:10]=[C:9]([Br:14])[CH:8]=1.Cl.C(OC=C)C>CCOCC>[CH2:5]([O:4][CH:1]([O:3][C:12]1[CH:11]=[CH:10][C:9]([Br:14])=[CH:8][CH:7]=1)[CH3:2])[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78084-BromophenolHCID 8023Ethyl vinyl etherHCID 8857Ethyl Acetate

Product 1

HCID 27237611-bromo-4-(1-ethoxyethoxy)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into 100 ml of dehydrated ethyl acetate, were fed 11.0 g (50 mmol) of p-bromophenol, and 4.8 ml of a solution composed of hydrochloric acid (1.0 mol/L) and ether, and the mixture was set at 40° C. Into the mixture, 10.8 g (150 mmol) of ethylvinylether was added dropwise, and the mixture was kept with stirring for one night. After completion of the reaction, the reaction solution was rinsed with sodium hydrogen carbonate solution and then rinsed with water to remove solvent. By purifying with silica gel column chromatography (eluate: hexane), 10.7 g (36.5 mmol) of 1-(1-ethoxy)ethoxy-4-bromobenzene was obtained.

Workup

  1. customwas set at 40° C
  2. customAfter completion of the reaction
  3. washthe reaction solution was rinsed with sodium hydrogen carbonate solution
  4. washrinsed with water
  5. customto remove solvent
  6. customBy purifying with silica gel column chromatography (eluate: hexane)

Sources & evidence

ORD record
ord-ffd1f9421537494f826ee392e6c85942
Source dataset
uspto-grants-2005_07
Patent number
US06921623B2

Reaction notes

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