4-Chlorobenzonitrile → 4-Fluorobenzonitrile

HRID 2396437Notes

Reaction equation

HRID 2396437 reaction equation
[F-:1].[K+].CC(CC(O)CO)C.Cl[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC.C1(C)C(C)=CC=CC=1>[F:1][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 121634-ChlorobenzonitrileHCID 911714-Methylpentane-1,2-diolHCID 522689Potassium Fluoride

Product 1

HCID 145174-Fluorobenzonitrile

Reagents, catalysts & solvents 2

HCID 76564Tetrabutylphosphonium bromideCatalystHCID 7237O-XyleneSolvent

Procedure

In a 250 ml flange flask and fitted with an impeller stirrer, 69.6 g (1.2 mol) of potassium fluoride, 6.9 g (0.02 mol) of tetrabutyl-phosphonium bromide, 13.8 g (0.02 mol) of dimethyldi(ethoxypolyoxypropyl)ammonium chloride, 13.8 g (0.028 mol) of polyethylene glycol dimethyl ether 500 and 20 g of xylene were metered at 120° C. into the melt of 137.6 g (1.0 mol) of 4-chlorobenzonitrile. After stirring for 30 minutes, the reaction suspension was azeotropically dried by distilling off the xylene under vacuum. The reaction suspension was stirred for 30 hours at 190° C. Amount of 4-fluorobenzonitrile formed: after 9 hours: 12 GC area-% after 30 hours: 48 GC area-%, besides 45 GC area-% of unreacted 4-chlorobenzonitrile.

Workup

  1. customIn a 250 ml flange flask and fitted with an impeller stirrer
  2. customthe reaction suspension was azeotropically dried
  3. distillationby distilling off the xylene under vacuum
  4. stirringThe reaction suspension was stirred for 30 hours at 190° C

Sources & evidence

ORD record
ord-3acca5cc29ea4e8c8a406ea32b2dcf15
Source dataset
uspto-grants-1996_02
Patent number
US05492875

Reaction notes

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