Nitric Acid → 1-(2,6-Difluoro-3-nitrophenyl)ethanone

HRID 571697

Reaction equation

HRID 571697 reaction equation
OS(O)(=O)=O.[N+:6]([O-:9])(O)=[O:7].[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=1[C:18](=[O:20])[CH3:19]>C(Cl)Cl>[F:10][C:11]1[C:16]([N+:6]([O-:9])=[O:7])=[CH:15][CH:14]=[C:13]([F:17])[C:12]=1[C:18](=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 836431-(2,6-Difluorophenyl)ethan-1-one

Product 1

HCID 138536371-(2,6-Difluoro-3-nitrophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

To a −40° C. mixture of concentrated H2SO4 (100 mL) and fuming HNO3 (100 mL) was added 1-(2,6-difluorophenyl)ethanone (20 g, 128 mmol) dropwise. The resulting mixture was stirred at −40° C. for 2 h then poured slowly onto ice. That mixture was diluted with DCM and the phases were separated. The aqueous layer was neutralized with sat. aq. NaHCO3 and then extracted with DCM. All organic portions were combined, dried over MgSO4, filtered, and concentrated to give 1-(2,6-difluoro-3-nitrophenyl)ethanone (26.3 g, 131 mmol, >theoretical) that was used without further purification.

Workup

  1. additionthen poured slowly onto ice
  2. customthe phases were separated
  3. extractionextracted with DCM
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fdffe23e2db44304b83f1530697be30a
Source dataset
uspto-grants-2015_05
Patent number
US09029362B2

Linked notes

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