Nitric Acid → HCID 14473250, compound

HRID 238949Notes

Reaction equation

HRID 238949 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]([F:16])([F:15])[F:14])[CH:7]=1>S(=O)(=O)(O)O>[F:5][C:6]1[CH:11]=[CH:10][C:9]([N+:1]([O-:4])=[O:2])=[C:8]([O:12][C:13]([F:14])([F:15])[F:16])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27772863-(Trifluoromethoxy)fluorobenzene

Product 1

HCID 14473250HCID 14473250, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

Fuming nitric acid (20 mL) was added dropwise to concentrated sulfuric acid (40 ml) under cooling (−10° C.), and subsequently, 1-fluoro-3-(trifluoromethoxy)benzene (15 g, 83 mmol) was added to the mixture at −10° C., and the mixture was stirred for 0.5 hours. After the mixture was added into ice-water to stop the reaction, it was extracted with dichloromethane. After the obtained organic layer was washed with a 1N aqueous sodium hydroxide solution and water, it was dried with anhydrous sodium sulfate. After filtration, the solution was concentrated and the residue was purified by silica gel column chromatography (100:0-97:3, hexane:ethyl acetate) to give the title compound (3.1 g, 16%) as an oil.

Workup

  1. customthe reaction, it
  2. extractionwas extracted with dichloromethane
  3. washAfter the obtained organic layer was washed with a 1N aqueous sodium hydroxide solution and water, it
  4. dry with materialwas dried with anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe solution was concentrated
  7. customthe residue was purified by silica gel column chromatography (100:0-97:3, hexane:ethyl acetate)

Sources & evidence

ORD record
ord-9055eb9eb43e47cf84ffecaf8ed26270
Source dataset
uspto-grants-2014_02
Patent number
US08642640B2

Reaction notes

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