2-Nitrophenol → 1-(3-Chloropropoxy)-4-nitrobenzene

HRID 2117618Notes

Reaction equation

HRID 2117618 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1O)([O-:3])=[O:2].[C:11](=[O:14])([O-])[O-].[K+].[K+].Br[CH:18]([Cl:21])[CH2:19]C>C(#N)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:14][CH2:11][CH2:19][CH2:18][Cl:21])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 36872Propane, bromochloro-

Product 1

HCID 118446171-(3-Chloropropoxy)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Nitrophenol (10 g, 72 mmol) was dissolved in acetonitrile (100 mL) and potassium carbonate (24.9 g, 180 mmol) added followed by bromochloropropane (113.2 g, 720 mmol). The mixture was heated and stirred under reflux overnight. The reaction was cooled to room temperature, the solid was then filtered off and the solvent evaporated under reduced pressure, taking care to remove all excess alkylating agent, to give the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationthe solid was then filtered off
  4. customthe solvent evaporated under reduced pressure
  5. customto remove all excess alkylating agent

Sources & evidence

ORD record
ord-63e72000e017408fad1fcfbdde73f0a5
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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