Acetic Acid → alpha-(2,4-difluorophenyl)-N-t-butylnitrone

HRID 636718

Reaction equation

HRID 636718 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]([N+:15]([O-])=[O:16])([CH3:14])[CH3:13].C(O)(=O)C>C(O)C.[Zn]>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[N+:15]([C:12]([CH3:14])([CH3:13])[CH3:11])[O-:16]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 116722-Methyl-2-nitropropaneHCID 737702,4-Difluorobenzaldehyde

Product 1

HCID 73770286alpha-(2,4-difluorophenyl)-N-t-butylnitrone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of 2,4-difluorobenzaldehyde (608.9 mg, 4.28 mmol), 1,1-dimethylnitroethane (881.9 mg, 8.55 mmol) and zinc (840.0 mg, 12.8 mmol) in ethanol (15 ml) was added acetic acid (1.54 g, 25.6 mmol) dropwise at 5° C. while stirring. The mixture was stirred at room temperature for one day. After the mixture was cooled to 5° C., zinc acetate was filtered off and the filtrate was concentrated and purified by silica gel chromatography (hexane/ethyl acetate=4/1).

Workup

  1. stirringThe mixture was stirred at room temperature for one day
  2. filtrationzinc acetate was filtered off
  3. concentrationthe filtrate was concentrated
  4. custompurified by silica gel chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-13e2320fe3994b55bbfbcaa192369478
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Linked notes

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