Hydrofluoric Acid → HCID 20325376, compound

HRID 1679155Notes

Reaction equation

HRID 1679155 reaction equation
[FH:1].[CH3:2][C:3]1([CH:9]=[CH:8][C:7]([F:10])=[C:6]([CH3:11])[CH2:5]1)N.N([O-])=O.[Na+]>CS(C)=O>[F:1][C:9]1[C:3]([CH3:2])=[CH:5][C:6]([CH3:11])=[C:7]([F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 14917Hydrofluoric Acid2×HCID 20325358HCID 20325358, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 20325376HCID 20325376, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.8 l of anhydrous hydrogen fluoride are initially introduced into a stirred vessel made of stainless steel and 625 g of 1,3-dimethyl-4-fluoro-aniline (see Am. Soc. 54, 2981) are introduced, whilst cooling. Subsequently, a diazotisation reaction is carried out, at 0° C, by adding 374 g of sodium nitrite in portions. The mixture is then slowly heated to room temperature. Since the splitting of the diazonium fluoride proceeds only slowly at this temperature, the temperature is raised up to the reflux temperature for hydrogen fluoride. Towards the end of the reaction 800 ml of dimethylsulphoxide are added and the temperature is further raised to 80° C and this temperature is maintained for 30 minutes. Subsequently, the reaction mixture is poured onto ice and extracted with methylene chloride and the organic phase is separated off, dried over sodium sulphate and then distilled. 428 g of 1,3-difluoro-4,6-dimethylbenzene with a boiling point of 143° C and a melting point of 30° to 31° C are obtained.

Workup

  1. additionare introduced
  2. temperaturewhilst cooling
  3. customSubsequently, a diazotisation reaction
  4. customis carried out, at 0° C
  5. additionare added
  6. temperaturethe temperature is further raised to 80° C
  7. temperaturethis temperature is maintained for 30 minutes
  8. additionSubsequently, the reaction mixture is poured onto ice
  9. extractionextracted with methylene chloride
  10. customthe organic phase is separated off
  11. dry with materialdried over sodium sulphate
  12. distillationdistilled

Sources & evidence

ORD record
ord-57c9ade27ed84304828f369bf757453f
Source dataset
uspto-grants-1978_03
Patent number
US04079089

Reaction notes

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