1-Chloro-2-nitrobenzene → 1-Fluoro-2-nitrobenzene

HRID 2260452Notes

Reaction equation

HRID 2260452 reaction equation
[F-:1].[K+].Cl[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11].C1(C)C(C)=CC=CC=1>[Cl-].C[N+](C)(C)C>[F:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 69451-Chloro-2-nitrobenzeneHCID 7237O-XyleneHCID 522689Potassium Fluoride

Product 1

HCID 738951-Fluoro-2-nitrobenzeneYield 63%

Reagents, catalysts & solvents 1

HCID 6379Tetramethylammonium chlorideCatalyst

Conditions

Temperature
150 °C

Procedure

In a 2-liter flange flask fitted with a distillation bridge and impeller stirrer, 348.6 g (6.0 mol) of potassium fluoride, 71.1 g (0.1 mol) of trimethyl (ethoxypolyoxypropyl)ammonium chloride and 23.5 g (0.21 mol) of tetramethylammonium chloride were introduced at 120° C. into the melt of 939 g (6.0 mol) of 2-chloronitrobenzene. Subsequently, 100 g (0.38 mol) of xylene were added and the reaction suspension was heated to 150° C., the xylene was removed under reduced pressure and the mixture was stirred for 21 hours at this temperature. Subsequently, the reaction suspension was cooled to 70° C. and filtered with suction. The salts separated off were washed twice with a total of 360 g of xylene and the combined organic phases were fractionated. 356 g (63% of theory) of 2-fluoronitrobenzene were isolated. Amount of 2-fluoronitrobenzene formed, according to GC analysis:

Workup

  1. customthe xylene was removed under reduced pressure
  2. temperatureSubsequently, the reaction suspension was cooled to 70° C.
  3. filtrationfiltered with suction
  4. customThe salts separated off
  5. washwere washed twice with a total of 360 g of xylene

Sources & evidence

ORD record
ord-c125a126ad5f4e8da58d13db9c88909e
Source dataset
uspto-grants-1995_12
Patent number
US05476976

Reaction notes

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