Potassium Carbonate → HCID 17755963, compound

HRID 491668Notes

Reaction equation

HRID 491668 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:11])=[C:8]([OH:10])[CH:9]=1)([O-:3])=[O:2].[CH3:12][O:13][CH2:14][CH2:15]Cl.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:11][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]=1[O:10][CH2:15][CH2:14][O:13][CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl etherHCID 692642-Chloro-5-nitrophenol

Product 1

HCID 17755963HCID 17755963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-nitro-2-chlorophenol (1.0 g, 5.8 mmol) and 2-methyloxychloroethane (2.6 mL, 28.8 mmol) in DMF (20 mL) was added K2CO3 (2.4 g, 17.4 mmol). The suspension was stirred at 80° C. for 18 h. After cooling, the mixture was filtered, the salts washed with EtOAc and the solvents removed under vacuum. The residue was dissolved in EtOAc and washed twice with NaOH (1 N) and once with H2O. The EtOAc layer was dried over MgSO4 and concentrated under vacuum. The crude was purified on silica gel using a Hexanes/EtOAc gradient (100/0 to 50/50) to give 1-chloro-2-(2-methoxy-ethoxy)-4-nitro-benzene.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. washthe salts washed with EtOAc
  4. customthe solvents removed under vacuum
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed twice with NaOH (1 N) and once with H2O
  7. dry with materialThe EtOAc layer was dried over MgSO4
  8. concentrationconcentrated under vacuum
  9. customThe crude was purified on silica gel using a Hexanes/EtOAc gradient (100/0 to 50/50)

Sources & evidence

ORD record
ord-87284b77cb92446d8976fc3dfc638cdb
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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