1,1-Dibromoethane → 1-(2-bromoethoxy)-2-chloro-4-nitrobenzene

HRID 1106864Notes

Reaction equation

HRID 1106864 reaction equation
[Br:1][CH:2](Br)[CH3:3].[Cl:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[OH:15]>C(=O)([O-])[O-].[K+].[K+].O>[Cl:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[O:15][CH2:3][CH2:2][Br:1]

Participants

5

Reactant 2

HCID 112011,1-DibromoethaneHCID 12074Nitrofungin

Product 1

HCID 3099731-(2-bromoethoxy)-2-chloro-4-nitrobenzeneYield 86.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
85 °C

Procedure

Dibromoethane (14.9 ml, 0.1728 mol) and 2-chloro-4-nitrophenol (10 g, 0.0576 mol) were dissolved in dimethylfomamide (250 ml) and potassium carbonate (9.55 g) was added to the resulting solution, followed by stirring at 85° C. for 30 min. Thereafter, the reaction solution was diluted with water and subjected to three extractions with ethyl acetate. The organic extracts were combined, dried with magnesium and the solvent was evaporated; thereafter, the residue was purified by being subjected to column chromatography using a 1:1 solvent system of n-hexane and ethyl acetate as an eluent and the fractions containing the end product were collected and subjected to evaporation to yield the end compound 1-(2-chloro-4-nitrophenoxy)-2-bromoethane (14.0 g) as a yellow solid mass.

Workup

  1. additionwas added to the resulting solution
  2. extractionsubjected to three extractions with ethyl acetate
  3. dry with materialdried with magnesium
  4. customthe solvent was evaporated
  5. customthereafter, the residue was purified
  6. additionthe fractions containing the end product
  7. customwere collected
  8. customsubjected to evaporation

Sources & evidence

ORD record
ord-e0c3fcc476fb47c5a5986c65e1824f45
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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