Nitric Acid → 1-Bromo-5-fluoro-4-nitro-2-(trifluoromethyl)benzene

HRID 1893475Notes

Reaction equation

HRID 1893475 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[N+:13]([O-])([OH:15])=[O:14].O>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:13]([O-:15])=[O:14])=[CH:4][C:3]=1[C:9]([F:12])([F:10])[F:11]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 27349092-Bromo-4-fluorobenzotrifluoride

Product 1

HCID 594197851-Bromo-5-fluoro-4-nitro-2-(trifluoromethyl)benzeneYield 92.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a stirred mixture of 2-bromo-4-fluorotrifluoromethylbenzene (33.7 g, 0.1387 mol) in sulfuric acid (98%, 34 mL) at 5° C. under nitrogen is added dropwise a mixture of sulfuric acid (98%, 10.1 mL) with fuming nitric acid (6.7 mL). The mixture is warmed up to room temperature for 2 hours and cooled down to 5° C. before adding water (60 mL). The resulting mixture is extracted twice with ethyl acetate (10 mL). The combined organic phases are washed with a saturated solution of sodium hydrogencarbonate (60 mL), water (60 mL) and dried over sodium sulfate. Concentration affords the title compound as a yellow solid (37.1 g, 92.9%)

Workup

  1. additionis added dropwise
  2. temperaturecooled down to 5° C.
  3. extractionThe resulting mixture is extracted twice with ethyl acetate (10 mL)
  4. washThe combined organic phases are washed with a saturated solution of sodium hydrogencarbonate (60 mL), water (60 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationConcentration

Sources & evidence

ORD record
ord-bee9b12423424c64b24b0c82cbf8d4fc
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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