1,2-Dibromoethane → 2-(2-Bromoethoxy)-3,4-difluoronitrobenzene

HRID 851078Notes

Reaction equation

HRID 851078 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:12].[Br:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:13][CH2:14][CH2:15][O:12][C:3]1[C:2]([F:1])=[C:7]([F:8])[CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 27337452,3-Difluoro-6-nitrophenol

Product 1

HCID 130600462-(2-Bromoethoxy)-3,4-difluoronitrobenzeneYield 60.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.9 g of the 2,3-difluoro-6-nitrophenol, 50.1 g of 1,2-dibromoethane and 18.7 g of potassium carbonate were added to 80 ml of dimethylformamide and the mixture was stirred for 2.5 hours at from about 80° to 100° C. (bath temperature). The reaction mixture was concentrated to dryness in vacuo and the residue was distributed between ethyl acetate and water. The organic solvent layer was washed with water and was dried, then the solvent was evaporated. The residue was dissolved in benzene and was purified by silica gel column chromatography to provide 7.7 g of 2-(2-bromoethoxy)-3,4-difluoronitrobenzene as light yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness in vacuo
  2. washThe organic solvent layer was washed with water
  3. customwas dried
  4. customthe solvent was evaporated
  5. dissolutionThe residue was dissolved in benzene
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-77c38893674a488c845c033e2c85bde3
Source dataset
uspto-grants-1983_05
Patent number
US04382892

Reaction notes

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