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

HRID 216491Notes

Reaction equation

HRID 216491 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 (3×). 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 (3×)
  3. dry with materialThe organic extracts are dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c1118a050ee448a9ddd7a9772d09438
Source dataset
uspto-grants-2012_06
Patent number
US08193229B2

Reaction notes

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