Hydrogen Peroxide → 2-(2-Fluorophenyl)isobutyramide

HRID 736445

Reaction equation

HRID 736445 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:12])([CH3:11])[C:9]#[N:10].[OH-:13].[Na+].OO>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:12])([CH3:11])[C:9]([NH2:10])=[O:13]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 119764412-(2-Fluorophenyl)-2-methylpropanenitrile

Product 1

HCID 119764962-(2-Fluorophenyl)isobutyramide

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

2-(2-Fluorophenyl)-2-methylpropionitrile (0.211 g) was magnetically stirred with aqueous solutions of 5N sodium hydroxide (2 mL), 55% tetrabutylammonium hydrogensulfate (0.1 mL) and 30% hydrogen peroxide (3 mL) for 22 hours. The reaction mixture was diluted with toluene and extracted. The aqueous phase was neutralized with 5% hydrochloric acid and extracted twice with ethyl acetate. The combined organic extracts were washed with water, then brine, and dried over anhydrous magnesium sulfate. Filtration and evaporation gave 2-(2-fluorophenyl)isobutyramide as a pale-green oil that solidified on standing (0.173 g). GC/MS: m/z 181 (RT 9.80 min.). 1H-NMR (DMSO-d6): 7.39-7.27 (m, 2H), 7.19-7.07 (m, 2H), 6.83 and 6.78 (2 s, CONH2), 1.43 (s, 6H)

Workup

  1. extractionextracted
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic extracts were washed with water
  4. dry with materialbrine, and dried over anhydrous magnesium sulfate
  5. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-efcc971d98ab4a76b3e31546f5e23bf2
Source dataset
uspto-grants-2009_09
Patent number
US07595338B2

Linked notes

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