Acetic Acid → alpha-(2,5-difluorophenyl)-N-t-butylnitrone

HRID 636742Notes

Reaction equation

HRID 636742 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([F:10])=[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]=[CH:8][C:7]([F:10])=[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 1376632,5-Difluorobenzaldehyde

Product 1

HCID 73691530alpha-(2,5-difluorophenyl)-N-t-butylnitroneYield 90%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2,5-difluorobenzaldehyde (291.5 mg, 2.05 mmol), 2-methyl-2-nitropropane (427.3 mg, 4.14 mmol) and zinc (407.3 mg, 6.23 mmol) in ethanol (5 ml) was cooled to 0° C. in ice-water bath. Acetic acid (0.69 ml, 12.0 mmol) was added dropwise to the mixture. The mixture was gradually warmed to room temperature, stirred for 2 hours and let stand overnight. The mixture was filtered through Celite® bed and the filtrate was concentrated and purified by silica gel chromatography (hexane/ethyl acetate=10/1) to give the title compound (393 mg; 90%).

Workup

  1. waitlet stand overnight
  2. filtrationThe mixture was filtered through Celite® bed
  3. concentrationthe filtrate was concentrated
  4. custompurified by silica gel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-19d3636b90254d51a310e94a9a0af4de
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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