p-Fluoronitrobenzene → HCID 4364549, compound

HRID 378857Notes

Reaction equation

HRID 378857 reaction equation
[OH-].[Na+].[CH3:3][C:4](=[N:6][OH:7])[CH3:5].F[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1>CN(C=O)C.[Cl-].[Na+].O>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([O:7][N:6]=[C:4]([CH3:5])[CH3:3])=[CH:10][CH:11]=1)([O-:17])=[O:16]

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 14798Sodium HydroxideHCID 67180Acetone, oxime

Product 1

HCID 4364549HCID 4364549, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a 0° C. slurry of sodium hydroxide (82 g, 2 mol) in DMF (1.5 L) was added acetone oxime (125 g, 1.7 mol). After stirring 45 min, 1-fluoro-4-nitrobenzene (218 g, 1.55 mol) was added over 45 min. After stirring at room temperature for 2.5 h, the reaction was poured into cold brine (4.5 L). The mixture was stirred at 0° C. for 2 h. The solid was collected by filtration, washed with water (4×1.5 L) and dried to provide 300 g (99%) of 2-propanone O-(4-nitrophenyl)oxime.

Workup

  1. stirringAfter stirring at room temperature for 2.5 h
  2. stirringThe mixture was stirred at 0° C. for 2 h
  3. filtrationThe solid was collected by filtration
  4. washwashed with water (4×1.5 L)
  5. customdried

Sources & evidence

ORD record
ord-557bd4012baa42c1a2410925b48fc80c
Source dataset
uspto-grants-2001_10
Patent number
US06297233B1

Reaction notes

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