2,5-Dichloronitrobenzene → HCID 18536021, compound

HRID 412131Notes

Reaction equation

HRID 412131 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](O)[CH:12]=[CH:13][CH:14]=1)[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:10]=[C:11]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[N+:24]([O-:26])=[O:25])[CH:12]=[CH:13][CH:14]=1)[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 138048Benzyl 3-hydroxyphenyl ether

Product 1

HCID 18536021HCID 18536021, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-(benzyloxy)phenol (1.145 g, 5.72 mmol) and 2,5-dichloronitrobenzene (1.154 g, 6.01 mmol) in 15 mL of DMSO was added cesium carbonate (3.72 g, 11.4 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-1e462c5bc2744b008f8050aa6339e958
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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