3,4-Dichlorophenol → 5-(3,4-Dichlorophenoxymethyl)-1,3-dinitrobenzene

HRID 431381Notes

Reaction equation

HRID 431381 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[CH2:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[C:14]([N+:21]([O-:23])=[O:22])[CH:13]=1>C(O)CCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[O:9][CH2:11][C:12]1[CH:13]=[C:14]([N+:21]([O-:23])=[O:22])[CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1

Participants

4

Reactant 2

HCID 72583,4-DichlorophenolHCID 94673Benzene, 1-(chloromethyl)-3,5-dinitro-

Product 1

HCID 187634315-(3,4-Dichlorophenoxymethyl)-1,3-dinitrobenzene

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

0.5 mmole 3,4-Dichloro-phenol and 1 mmole KI were added to a solution of 0.5 mmole 1-Chloromethyl-3,5-dinitrobenzene in 2.5 ml 1-Butanol. The mixture was stirred under reflux overnight. After evaporation the 1-Butanol, the residue was washed with 2×10 ml 1 N HCl and 2×10 ml EtOAc, and dried. 1H NMR (DMSO-d6, 400 MHz) 5.44 (s, 2H); 7.14 (d, 1H); 7.43 (s, 1H); 7.58 (d, 1H); 8.73 (s, 2H); 8.81 (s, 1H);

Workup

  1. temperatureunder reflux overnight
  2. customAfter evaporation the 1-Butanol
  3. washthe residue was washed with 2×10 ml 1 N HCl and 2×10 ml EtOAc
  4. customdried

Sources & evidence

ORD record
ord-6baf92297a254d29ab178887814f1c0f
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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