Nitric Acid → 2,6-Difluoro-3-nitro-phenylacetamide

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]#[N:11].[N+:12]([O-])([OH:14])=[O:13].[OH:16]S(O)(=O)=O>>[F:1][C:2]1[C:7]([N+:12]([O-:14])=[O:13])=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]([NH2:11])=[O:16]

Participants

Reactant 3

HCID 944Nitric Acid

HCID 1118Sulfuric Acid2×

HCID 69559(2,6-Difluorophenyl)acetonitrile

Product 1

HCID 684632402,6-Difluoro-3-nitro-phenylacetamide

Procedure

To a stirred mixture 2,6-difluorophenylacetonitrile (3.06 g, 20.0 mmol) in 30 mL of H2SO4 at 0° C. was added 12 mL of a 1:1 mixture of nitric acid and sulfuric acid. The reaction mixture stirred for 5 h and poured onto crushed ice. The resulting solid was filtered and air dried to give 2,6-difluoro-3-nitro-phenylacetamide.