1,2-Dibromoethane → 2-(2-Bromo-ethoxy)-1-chloro-4-nitrobenzene

HRID 914967Notes

Reaction equation

HRID 914967 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[Br:12][CH2:13][CH2:14]Br.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:12][CH2:13][CH2:14][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 692642-Chloro-5-nitrophenol

Product 1

HCID 3097182-(2-Bromo-ethoxy)-1-chloro-4-nitrobenzeneYield 42.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-chloro-5-nitro-phenol (13, 0.87 g, 5 mmol) in acetone (10 mL) were sequentially added 1,2-dibromoethane (14, 0.85 ml, 10 mmol) and K2CO3 (1.45 g, 10.5 mmol). The mixture was heated under reflux over night. To work up, the solids were filtered and the filtrate was concentrated. The residue was purified by chromatography (silica gel) eluting with hexanes first, then EtOAc to yield 15 (600 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux over night
  3. filtrationthe solids were filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography (silica gel)
  6. washeluting with hexanes first

Sources & evidence

ORD record
ord-8a9e81af75e048819d47722fd5b17a5f
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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