1,2-Dichloro-4-nitrobenzene → 2-Chloro-1-(4-chlorobenzyloxy)-4-nitrobenzene

HRID 1361467Notes

Reaction equation

HRID 1361467 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[Cl:11].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[Cl:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[O:18][CH2:17][C:16]1[CH:19]=[CH:20][C:13]([Cl:12])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 74431,2-Dichloro-4-nitrobenzeneHCID 11430Potassium CarbonateHCID 133974-Chlorobenzyl alcohol

Product 1

HCID 669219222-Chloro-1-(4-chlorobenzyloxy)-4-nitrobenzeneYield 46.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

N,N-Dimethylacetamide (42 mL), 16.2 g of 1,2-dichloro-4-nitrobenzene, 12 g of 4-chlorobenzyl alcohol, and 8.7 g of potassium carbonate were mixed together, and the mixture was stirred with heating at 100 to 140° C. for 30 hr. This reaction solution was concentrated under the reduced pressure. The residue was dissolved in 100 mL of ethyl acetate and 100 mL of toluene, and the solution was washed with water and brine. The organic layer was concentrated under the reduced pressure, and the residue was recrystallized from ethanol to give 11.77 g of 2-chloro-1-(4-chlorobenzyloxy)-4-nitrobenzene (yield 46.9%).

Workup

  1. concentrationThis reaction solution was concentrated under the reduced pressure
  2. dissolutionThe residue was dissolved in 100 mL of ethyl acetate
  3. wash100 mL of toluene, and the solution was washed with water and brine
  4. concentrationThe organic layer was concentrated under the reduced pressure
  5. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-8f3e5a6aa3a64f26a10b7bddc406421d
Source dataset
uspto-grants-2011_02
Patent number
US07880006B2

Reaction notes

Loading…