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

HRID 2292247Notes

Reaction equation

HRID 2292247 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1Cl.CS(C)=O.C1C=CC=CC=1.[F-:22].[K+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:22]

Participants

6

Reactant 4

HCID 241BenzeneHCID 679Dimethyl SulfoxideHCID 74431,2-Dichloro-4-nitrobenzeneHCID 522689Potassium Fluoride

Product 1

HCID 676882-Chloro-1-fluoro-4-nitrobenzeneYield 63.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 g of 3,4-dichloro-nitro benzene were added to a mixture of 120 ml of dimethylsulfoxide, 80 ml of benzene and 35 g of potassium fluoride and the mixture was stirred at 180°-185° C. for two hours. 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 a pressure of 3 to 4 mm Hg. The residue was rectified at a pressure of 15 mm Hg to obtain 29 g of 3-chloro-4-fluoro-nitrobenzene melting at 41° to 43° C.

Workup

  1. extractionthe distillate was extracted with isopropyl ether
  2. customThe combined organic phases were dried
  3. distillationdistilled at 40° C. under a pressure of 3 to 4 mm Hg

Sources & evidence

ORD record
ord-48cb82761dbc4cb3bce58158f83e8a10
Source dataset
uspto-grants-1989_01
Patent number
US04801717

Reaction notes

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