2,5-Dichloronitrobenzene → HCID 18536196, compound

HRID 412125Notes

Reaction equation

HRID 412125 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25].C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 69772,5-DichloronitrobenzeneHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 804592-Benzyloxyphenol

Product 1

HCID 18536196HCID 18536196, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-(benzyloxy)phenol (4.2736 g, 21.34 mmol) and 2,5-dichloronitrobenzene (4.302 g, 22.41 mmol) in 40 mL of DMSO was added cesium carbonate (13.8 g, 42.7 mmol). The reaction was heated to 70° C. under argon for one hour, then cooled to room temperature. The solution was poured into EtOAc, washed with water, sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The titled product was obtained as a brown oil.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with water, sat. aq. NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a8a4587e13f34d03bd13cfcbdcd4b924
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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