Water → 4-Nitro-2-(trifluoromethyl)anisole

HRID 2222751Notes

Reaction equation

HRID 2222751 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].C[O-].[Na+].O.[C:19](OCC)(=[O:21])C>O1CCCC1>[CH3:19][O:21][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 949542-Fluoro-5-nitrobenzotrifluorideHCID 10942334Sodium Methoxide

Product 1

HCID 695624-Nitro-2-(trifluoromethyl)anisole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-Fluoro-4-nitro-2-trifluoromethylbenzene 67 (0.1 mol), was dissolved in tetrahydrofuran (100 mL). The solution was cooled to 0° C. and sodium methoxide (0.1 mol) was added. The reaction was warmed to room temperature over 2 hours. Water and ethyl acetate were added. The organic phase was dried and concentrated to afford 1-methoxy-4-nitro-2-trifluoromethylbenzene 68. This material was dissolved in methylene chloride (100 mL) and the solution was cooled to −78° C. Boron tribromide (0.1 mol) was added. The mixture was warmed to room temperature. Water was added, and the organic phase was dried and concentrated. Chromatography then afforded the title compound 69.

Workup

  1. temperatureThe reaction was warmed to room temperature over 2 hours
  2. customThe organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-57d152175c9948eb8b05c7d702d35f8c
Source dataset
uspto-grants-2008_05
Patent number
US07371888B2

Reaction notes

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