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

HRID 1880263Notes

Reaction equation

HRID 1880263 reaction equation
CN(C=O)C.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-dinitrobenzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

DMF (10 ml) and thionyl chloride (14 ml) are added successively to 4-fluoro-2,6-dinitrophenol (26.00 g) in benzene (50 ml). The resulting solution is stirred at room temperature for 5 min (an intermediate precipitates) and then heated under reflux for 1.5 h (or until the starting material has reacted completely). The reaction mixture is cooled to room temperature, concentrated and the residue is poured onto ice/water. The precipitate is collected by filtration, washed three times with water and dried. After recrystallization from ethanol 23.50 g (83% of theory) of product are obtained in crystalline form.

Workup

  1. customprecipitates) and
  2. temperaturethen heated
  3. temperatureunder reflux for 1.5 h (or until the starting material
  4. customhas reacted completely)
  5. temperatureThe reaction mixture is cooled to room temperature
  6. concentrationconcentrated
  7. additionthe residue is poured onto ice/water
  8. filtrationThe precipitate is collected by filtration
  9. washwashed three times with water
  10. customdried
  11. customAfter recrystallization from ethanol 23.50 g (83% of theory) of product
  12. customare obtained in crystalline form

Sources & evidence

ORD record
ord-0ff7d2db8f47427d994fa0c81fd18818
Source dataset
uspto-grants-2012_11
Patent number
US08318761B2

Reaction notes

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