1,3-Dinitrobenzene → 3-(4-Chloro-3-ethylphenoxy)-1-nitrobenzene

HRID 1265191Notes

Reaction equation

HRID 1265191 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1)([O-])=O.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=1[CH2:21][CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:4]2[CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:8][CH:9]=2)=[CH:16][C:15]=1[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 74521,3-DinitrobenzeneHCID 10796Cesium carbonateHCID 842234-Chloro-3-ethylphenol

Product 1

HCID 110657543-(4-Chloro-3-ethylphenoxy)-1-nitrobenzeneYield 78.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

EX-8A) To a solution of 1,3-dinitrobenzene (16.8 g, 0.1 mol) and 4-chloro-3-ethylphenol (15.6 g, 0.1 mol) in 200 mL of dimethylsulfoxide was added cesium carbonate (65 g, 0.2 mol). The reaction mixture was heated at 100° C. under nitrogen overnight then cooled to room temperature. The reaction mixture was filtered through cemete then rins ed with diethyl eth er and a small amount of water. The filtrate was extracted several times with diethyl ether. The organic layers were combined, washed with water and brine, dried over MgSO4, and concentrated in vacuo to give 21.8 g (78%) of the desired 3-(4-chloro-3-ethylphenoxy)-1-nitrobenzene product as a dark orange oil, which was greater than 90% pure by reverse phase HPLC analysis. HRMS calcd. for C14H12ClNO3: 295.0849 [M+NH4]+, found 295.0862.

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationThe reaction mixture was filtered through cemete
  3. extractionThe filtrate was extracted several times with diethyl ether
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a431b2d6d344b61a511030d42890ab3
Source dataset
uspto-grants-2003_04
Patent number
US06544974B2

Reaction notes

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