4-Fluoro-3-nitroaniline → 2,4-difluoro-N-(4-fluoro-3-nitrophenyl)benzamide

HRID 1591863

Reaction equation

HRID 1591863 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[F:12][C:13]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16]>O1CCOCC1>[F:12][C:13]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:14]=1[C:15]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)=[O:16]

Participants

4

Reactant 2

HCID 677684-Fluoro-3-nitroanilineHCID 5880812,4-Difluorobenzoyl chloride

Product 1

HCID 92126042,4-difluoro-N-(4-fluoro-3-nitrophenyl)benzamideYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using a method similar to Preparation 13, using 4-fluoro-3-nitroaniline (1.0 g, 6.4 mmol), dioxane (20 mL), and 2,4-difluorobenzoyl chloride (1.46 g, 8.3 mmol) gives the title intertermediate (1.6 g, 84% yield): mass spectrum (ion spray): m/z=297.0 (M+1).

Workup

  1. customsimilar to Preparation 13
  2. customgives the title intertermediate (1.6 g, 84% yield)

Sources & evidence

ORD record
ord-b508ae27cc934c9096a95eaf571eabde
Source dataset
uspto-grants-2007_11
Patent number
US07291632B2

Linked notes

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