Nitric Acid → 1-Chloro-4-fluoro-2-methyl-5-nitrobenzene

HRID 515298Notes

Reaction equation

HRID 515298 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[CH3:18]>>[Cl:10][C:11]1[CH:16]=[C:15]([N+:6]([O-:9])=[O:7])[C:14]([F:17])=[CH:13][C:12]=1[CH3:18]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 1184752-Chloro-5-fluorotoluene

Product 1

HCID 103524921-Chloro-4-fluoro-2-methyl-5-nitrobenzeneYield 79.7%

Procedure

To concentrated sulfuric acid (23.81 g), cooled to 0° C., under a nitrogen atmosphere, was added concentrated nitric acid (27.5 g) dropwise. 2-Chloro-5-fluorotoluene (9 g) was added dropwise and the reaction was stirred for 2 hours. The reaction was poured into ice and extracted with ethyl acetate. The organic phase was washed with aqueous sodium hydrogen carbonate, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica column chromatography [eluting with ethyl acetate/heptane (1:2)] to yield the title compound (9.4 g).

Workup

  1. additionThe reaction was poured into ice
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with aqueous sodium hydrogen carbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica column chromatography [eluting with ethyl acetate/heptane (1:2)]

Sources & evidence

ORD record
ord-b8ae0185407d4e0daab5b30d35431734
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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