4-Nitrophenol → 1-(2-Bromoethoxy)-4-nitrobenzene

HRID 1729125Notes

Reaction equation

HRID 1729125 reaction equation
[Na].[CH:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([OH:11])[CH:3]=1.[Br:12][CH:13](Br)[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:12][CH2:13][CH2:14][O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 5360545Sodium

Product 1

HCID 2359871-(2-Bromoethoxy)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.97 g of the sodium salt of p-nitrophenol(0.01 mol), 2.16 ml of dibromoethane (0.025 mol) and 0.5g of potassium carbonate were taken in 50 ml of dry acetone (4A activated molecular sieves) and refluxed overnight. Potassium carbonate was filtered and the solvent was removed by rotary evaporation to yield 4-(2-bromoethoxy)nitrobenzene (L) in almost quantitative yield. 1H-NMR: CDCl w: 365 (t,2H), 44 (t,2H), 70-83 (ABq,4H)/

Workup

  1. temperaturerefluxed overnight
  2. filtrationPotassium carbonate was filtered
  3. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-95bfdcc4e8164edd9b866f8af5f1933b
Source dataset
uspto-grants-1994_07
Patent number
US05332662

Reaction notes

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