Dimethylformamide → HCID 86755366, compound

HRID 1106879Notes

Reaction equation

HRID 1106879 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[Br:12][CH2:13][CH2:14]Br.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH2:14][CH2:13][Br:12]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 221092-Bromo-4-nitrophenol

Product 1

HCID 86755366HCID 86755366, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
82.5 °C

Procedure

A portion (2.3 g, 10.6 mmol) of the 2-bromo-4-nitrophenol produced in (1) above and 1,2-dibromoethane (7.9 g, 42.1 mmol) were added to N,N-dimethylformamide (20 ml); to the mixture, potassium carbonate (1.6 g) was added, followed by stirring at 80-85° C. for 3 h. The reaction mixture was added to water (100 ml) and extraction was conducted with ethyl acetate, followed by the drying of the extract with magnesium sulfate and concentration. The residue was subjected to column chromatography using a 10:3:1 solvent system of n-hexane, ethyl ether and ethyl acetate as an eluent to yield the end compound 1-(2-bromo-4-nitrophenoxy-2-bromoethane (2.14 g).

Workup

  1. customdrying of the
  2. extractionextract with magnesium sulfate and concentration

Sources & evidence

ORD record
ord-6857e1eefdbc4824b96790698ff4583c
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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