Nitric Acid → 5-Chloro-2-(2,3-difluoro-6-methoxybenzyloxy)-4-nitroanisole

HRID 1512969Notes

Reaction equation

HRID 1512969 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=2[F:21])=[C:6]([O:8][CH3:9])[CH:7]=1.[N+:22]([O-])([OH:24])=[O:23].O>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[C:3]([N+:22]([O-:24])=[O:23])=[CH:4][C:5]([O:10][CH2:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=2[F:21])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 593099945-Chloro-2-(2,3-difluoro-6-methoxybenzyloxy)anisole

Product 1

HCID 593097415-Chloro-2-(2,3-difluoro-6-methoxybenzyloxy)-4-nitroanisole

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a suspension of 5-chloro-2-(2,3-difluoro-6-methoxybenzyloxy)anisole (8.6 g) in acetic anhydride (54 mL) was added 60% nitric acid (2.9 mL) in a dropwise manner under ice-cooling, and the mixture was stirred under ice-cooling for 30 minutes. To the reaction mixture was added water (54 mL) in a dropwise manner, and the resulting mixture was stirred under ice-cooling for 30 minutes. The precipitated crystals were collected by filtration. The collected crystals were washed with water and a mixed solvent (n-hexane/ethanol=4/1), and dried under reduced pressure to give the title compound (9.41 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. stirringthe resulting mixture was stirred under ice-
  4. temperaturecooling for 30 minutes
  5. filtrationThe precipitated crystals were collected by filtration
  6. washThe collected crystals were washed with water
  7. dry with materiala mixed solvent (n-hexane/ethanol=4/1), and dried under reduced pressure

Sources & evidence

ORD record
ord-e9ad5f3645264bbc8350c488a8fd912c
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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