Nitric Acid → 3-Chloro-2,4-difluoro-5-nitrobenzoic acid

HRID 1176917Notes

Reaction equation

HRID 1176917 reaction equation
[Cl:1][C:2]1[C:3]([F:12])=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=[O:6].OS(O)(=O)=O.[N+:18]([O-])([OH:20])=[O:19]>>[Cl:1][C:2]1[C:3]([F:12])=[C:4]([CH:8]=[C:9]([N+:18]([O-:20])=[O:19])[C:10]=1[F:11])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 27735323-Chloro-2,4-difluorobenzoic acid

Product 1

HCID 155499183-Chloro-2,4-difluoro-5-nitrobenzoic acidYield 95%

Procedure

3-Chloro-2,4-difluoro-benzoic acid 1a (3.00 g, 15.6 mmol) is added to a stirred solution of concentrated H2SO4 (16 mL) and fuming nitric acid (0.85 mL, 20.3 mmol). After 3 hours a precipitate forms. The yellow slurry is poured onto ice water (100 mL). The aqueous mixture is extracted with diethyl ether (333 ). The organic extracts are dried (Na2SO4) and concentrated under reduced pressure to give 3.50 g (95%) of clean desired product as a pale yellow solid.

Workup

  1. additionThe yellow slurry is poured onto ice water (100 mL)
  2. extractionThe aqueous mixture is extracted with diethyl ether (333 )
  3. dry with materialThe organic extracts are dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-612a91a0ba114a17ba1fb23cd4f55b4c
Source dataset
uspto-grants-2010_11
Patent number
US07842816B2

Reaction notes

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