Dimethylformamide → 2-Chloro-5-fluoro-1,3-dinitrobenzene

HRID 901881Notes

Reaction equation

HRID 901881 reaction equation
CN(C)C=O.S(Cl)([Cl:8])=O.[F:10][C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[C:14](O)=[C:13]([N+:21]([O-:23])=[O:22])[CH:12]=1>C1C=CC=CC=1>[Cl:8][C:14]1[C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:11]([F:10])=[CH:12][C:13]=1[N+:21]([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 94951Phenol, 4-fluoro-2,6-dinitro-

Product 1

HCID 123611032-Chloro-5-fluoro-1,3-dinitrobenzeneYield 98.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 1.9 mL (24.74 mmol) of dimethyl formamide dissolved in 20 mL benzene was added 2.7 mL (37.11 mmol) thionyl chloride. The mixture was stirred for 10 minutes and 5.0 g (24.74 mmol) 4-fluoro-2,6-dinitrophenol was added. The mixture was refluxed 6 hours, cooled and concentrated under reduced pressure. The residue was recrystallized from ethanol to give 2-chloro-5-fluoro-1,3-dinitro-benzene (5.39 g).

Workup

  1. temperatureThe mixture was refluxed 6 hours
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-44dc63b79abb472596dfa4f1c8f80d4a
Source dataset
uspto-grants-2008_04
Patent number
US07365063B2

Reaction notes

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