Water → Benzonitrile, 2-chloro-3-fluoro-6-(trifluoromethyl)-

HRID 1005489Notes

Reaction equation

HRID 1005489 reaction equation
F[C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:3]=1[C:4]#[N:5].[Cl-:15].[Ca+2].[Cl-].O>CS(C)=O>[Cl:15][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 101044562,3-Difluoro-6-(trifluoromethyl)benzonitrile

Product 1

HCID 15452061Benzonitrile, 2-chloro-3-fluoro-6-(trifluoromethyl)-Yield 70.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
145 °C

Procedure

To a solution of 50.9 g of 2,3-difluoro-6-trifluoromethylbenzonitrile in 240 ml of dimethyl sulfoxide (DMSO) was added 53.3 g of calcium chloride and the mixture was stirred for 6 hours at a temperature of from 140 to 150° C. After cooling, the reaction mixture was further added with 240 ml water and extracted with 240 ml and 100 ml hexane twice. The organic layer obtained was dried over anhydrous magnesium sulfate, and the solvent therein was distilled under reduced pressure. The crude product obtained was distilled under reduced pressure to obtain 38.9 g of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with 240 ml and 100 ml hexane twice
  3. customThe organic layer obtained
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationthe solvent therein was distilled under reduced pressure
  6. customThe crude product obtained
  7. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-c6dd330d517d438d9add348fb60ff564
Source dataset
uspto-grants-2000_04
Patent number
US06054605

Reaction notes

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