4-Nitrophenol → 1-(4-Chloro-butoxy)-4-nitrobenzene

HRID 2240041Notes

Reaction equation

HRID 2240041 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:12][CH2:13][CH2:14][CH2:15][Cl:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:16][CH2:15][CH2:14][CH2:13][CH2:12][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutane

Product 1

HCID 145719461-(4-Chloro-butoxy)-4-nitrobenzeneYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of para-nitrophenol (0.83 g, 6 mmoles), 1-bromo-4-chloro-butane (1.23 g, 7.2 mmoles), and K2CO3 (1.24 g, 9 mmoles) was stirred together in DMF at 80° C. for 1 hour. Reaction mixture was diluted with H2O, extracted with EtOAc, washed with water (2×), brine (1×), dried over Na2SO4, and concentrated under vacuum. The crude product was purified by HPLC using as eluent 30% EtOAc/hexane to afford the title compound as an off-white solid (1.28 g, 5.6 mmoles).

Workup

  1. customReaction mixture
  2. extractionextracted with EtOAc
  3. washwashed with water (2×), brine (1×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-b95f302e594c4c958d77ccf35bc5fd3a
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

Loading…