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

HRID 1106856Notes

Reaction equation

HRID 1106856 reaction equation
[Br:1][CH2:2][CH2:3]Br.[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)([O-:7])=[O:6].[OH-].[Na+]>C(O)C>[N+:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:3][CH2:2][Br:1])=[CH:10][CH:9]=1)([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 78391,2-DibromoethaneHCID 14798Sodium Hydroxide

Product 1

HCID 2359871-(2-Bromoethoxy)-4-nitrobenzeneYield 50.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,2-Dibromoethane (24.4 g, 0.13 mol) and 4-nitrophenol (6 g, 0.044 mol) were dissolved in ethyl alcohol (60 ml) and sodium hydroxide (2 g) was added to the solution. The reaction mixture was refluxed for 24 h and thereafter concentrated under vacuum, followed by column chromatography using a 3:1 solvent system of n-hexane and ethyl acetate as an eluent to yield the end compound 1-(4-nitrophenoxy) -2-bromoethane (5.5 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 24 h
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8a528f6ed9654189aebc5a279bf33c29
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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