4-Fluorophenol → Methyl 3-(4-fluorophenoxy)-5-nitrobenzoate

HRID 873494

Reaction equation

HRID 873494 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])([O-])=O.[F:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[F:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:4]2[CH:5]=[C:6]([CH:11]=[C:12]([N+:14]([O-:16])=[O:15])[CH:13]=2)[C:7]([O:9][CH3:10])=[O:8])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 62657Potassium Phosphate, TribasicHCID 222067Methyl 3,5-dinitrobenzoate

Product 1

HCID 86730099Methyl 3-(4-fluorophenoxy)-5-nitrobenzoateYield 79.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The compound prepared in Example 34 (4.73 g) was dissolved in DMF (40 mL), added with 4-fluorophenol (2.34 g) and potassium phosphate (5.32 g) and stirred overnight at 80° C. The reaction solution was diluted with ethyl acetate, sequentially washed with water and a saturated sodium chloride solution and dried over anhydrous magnesium sulphate before distillation of the solvent. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1→1:1) to give the titled compound (4.81 g) having the following physical properties.

Workup

  1. washsequentially washed with water
  2. dry with materiala saturated sodium chloride solution and dried over anhydrous magnesium sulphate before distillation of the solvent
  3. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1→1:1)

Sources & evidence

ORD record
ord-7ff8e089745a4b96ba87d50a6b81581d
Source dataset
uspto-grants-2015_03
Patent number
US08975409B2

Linked notes

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