4-Fluoro-2-isopropoxy-1-nitrobenzene → HCID 20701061, compound

HRID 518876Notes

Reaction equation

HRID 518876 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1.[CH3:15][O-:16].[Na+]>CO>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:16][CH3:15])=[CH:3][C:4]=1[O:11][CH:12]([CH3:14])[CH3:13])([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 106318324-Fluoro-2-isopropoxy-1-nitrobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 20701061HCID 20701061, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 5.0 g of 4-fluoro-1-nitro-2-(propan-2-yloxy)benzene, 4.07 g of sodium methoxide and 200 mg of 18C6 in 100 ml of methanol is heated at 65° C. for 2 h. The mixture is then concentrated and the residue is taken up with a mixture of water and ethyl acetate. The aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried over anhydrous magnesium sulfate, filtered and then concentrated to dryness under reduced pressure, so as to obtain 5.0 g of 1-nitro-4-methoxy-2-(propan-2-yloxy)benzene.

Workup

  1. concentrationThe mixture is then concentrated
  2. additionthe residue is taken up with a mixture of water and ethyl acetate
  3. extractionThe aqueous phase is extracted three times with ethyl acetate
  4. dry with materialThe combined organic phases are dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-3b4464bbfc9949be8d796e1757dc8e3f
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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