5-Chloro-2-nitrobenzotrifluoride → 5-Methoxy-2-nitrobenzotrifluoride

HRID 1713685Notes

Reaction equation

HRID 1713685 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:15][O-:16].[Na+]>>[CH3:15][O:16][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

3

Reactant 2

HCID 670525-Chloro-2-nitrobenzotrifluorideHCID 10942334Sodium Methoxide

Product 1

HCID 5485175-Methoxy-2-nitrobenzotrifluoride

Procedure

A mixture of 5-chloro-2-nitrobenzotrifluoride (5 g, 22.2 mmol) and 0.5M NaOMe (in MeOH) is stirred for 15 h at reflux. After removal of the solvent, the residue is diluted with H2O (40 mL) and extracted with CH2Cl2 (3×150 mL). The organic phase is washed with H2O (30 mL), and brine (30 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound: ES-MS: 221.0 [M]−; single peak at tR=4.72 min (System 2).

Workup

  1. temperatureat reflux
  2. customAfter removal of the solvent
  3. additionthe residue is diluted with H2O (40 mL)
  4. extractionextracted with CH2Cl2 (3×150 mL)
  5. washThe organic phase is washed with H2O (30 mL), and brine (30 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f98be2a81f964f71a975d02b47fad734
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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