1-Bromo-2-Chloroethane → 4-(2-Chloroethoxy)-1-methoxy-2-nitrobenzene

HRID 1042705Notes

Reaction equation

HRID 1042705 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][Cl:22]>C(#N)C>[Cl:22][CH2:21][CH2:20][O:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 149589074-Methoxy-3-nitrophenol

Product 1

HCID 594278584-(2-Chloroethoxy)-1-methoxy-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Methoxy-3-nitrophenol (0.8 g, 4.7 mmol) was dissolved in acetonitrile (13 ml). Potassium carbonate (1.63 g, 11.8 mmol) was added, followed by 1-bromo-2-chloroethane (3.93 ml, 47.2 mmol). The reaction was heated and stirred at reflux for 20 h. The reaction was cooled to room temperature, the solid was then filtered off and the solvent evaporated under reduced pressure to give the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 20 h
  3. filtrationthe solid was then filtered off
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-182ee304c37446a5abf409aff4fd9888
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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