Hydrofluoric Acid → 2-Fluoro-m-xylene

HRID 1464713Notes

Reaction equation

HRID 1464713 reaction equation
ClC(O[C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:12])=O.[FH:13]>>[CH3:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:5]=1[F:13]

Participants

3

Reactant 2

HCID 14917Hydrofluoric AcidHCID 2716182,6-Dimethylphenyl carbonochloridate

Product 1

HCID 1230652-Fluoro-m-xyleneYield 69%

Conditions

Temperature
130 °C

Procedure

2000 ml of anhydrous hydrogen fluoride were placed at 0° in a stainless steel laboratory autoclave and 500 g of 2,6-dimethylphenyl chloroformate were added dropwise. The autoclave was then sealed and heated at a maximum temperature of 130° C. for 3 hours. The pressure of the gases evolved was released at 26 bar. The autoclave was then cooled to room temperature and the excess hydrogen fluoride was distilled off. The remaining reaction mixture was poured onto ice and the organic phase was separated off and distilled under vacuum. 2,6-Dimethylfluorobenzene was obtained in a yield of 69%.

Workup

  1. additionwere added dropwise
  2. customThe autoclave was then sealed
  3. temperatureThe autoclave was then cooled to room temperature
  4. distillationthe excess hydrogen fluoride was distilled off
  5. customThe remaining reaction mixture
  6. additionwas poured onto ice
  7. customthe organic phase was separated off
  8. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-a8a4e111f5ee4e41ad67b8ec08e03bda
Source dataset
uspto-grants-1994_04
Patent number
US05306849

Reaction notes

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