Nitric Acid → 2-Fluoro-5-methoxycarbonyloxy-4-methylnitrobenzene

HRID 1691811Notes

Reaction equation

HRID 1691811 reaction equation
[CH3:1][O:2][C:3](=[O:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[CH3:12].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:13])[O:4][C:5]1[CH:10]=[C:9]([N+:14]([O-:16])=[O:15])[C:8]([F:11])=[CH:7][C:6]=1[CH3:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 106790444-Fluoro-2-methylphenyl Methoxyformate

Product 1

HCID 144216192-Fluoro-5-methoxycarbonyloxy-4-methylnitrobenzeneYield 50.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

Carbonic acid 4-fluoro-2-methyl-phenyl ester methyl ester (12.8 g, 69.5 mmol) was suspended in 8 ml of concentrated sulfuric acid and cooled to 0° C. A mixture of concentrated nitric acid (8 ml) in concentrated sulfuric acid (8 ml) was added slowly, maintaining a reaction temperature below 50° C. After addition the mixture was stirred for 2 hours. The reaction mixture was poured into ice-water, forming a precipitate which was filtered and dried to give carbonic acid 4-fluoro-2-methyl-5-nitro-phenyl ester methyl ester (8.0 g, 50.3%) as a white powder.

Workup

  1. additionwas added slowly
  2. temperaturemaintaining a reaction temperature below 50° C
  3. additionAfter addition the mixture
  4. customforming a precipitate which
  5. filtrationwas filtered
  6. customdried

Sources & evidence

ORD record
ord-6186cbb152bd43f1a4906570f827abaa
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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