Benzene → 4-Chloro-1-fluoro-2-nitrobenzene

HRID 2292248Notes

Reaction equation

HRID 2292248 reaction equation
CS(C)=O.C1C=CC=CC=1.[F-:11].[K+].Cl[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22]>O>[F:11][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 241BenzeneHCID 679Dimethyl SulfoxideHCID 69772,5-DichloronitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 676604-Chloro-1-fluoro-2-nitrobenzeneYield 22.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 120 ml of dimethylsulfoxide, 80 ml of benzene, 35 g of potassium fluoride and 50 g of 2,5-dichloronitrobenzene was heated with stirring to 140° C. and was then heated at 180°-185° C. for three hours and then cooled. The water vapor was entrained and the distillate was extracted with isopropyl ether. The combined organic phases were dried and distilled at 40° C. under reduced pressure and were rectified at 14 mm Hg to obtain 10.1 g of 2-fluoro-5-chloro-nitrobenzene with a refractive index of nD20 =1.5558.

Workup

  1. temperaturewas heated
  2. temperaturewas then heated at 180°-185° C. for three hours
  3. temperaturecooled
  4. extractionthe distillate was extracted with isopropyl ether
  5. customThe combined organic phases were dried
  6. distillationdistilled at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-7c986cb29c9d413ba7004549991eac0b
Source dataset
uspto-grants-1989_01
Patent number
US04801717

Reaction notes

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