Hydrofluoric Acid → HCID 20325376, compound

Participants

Reaction Steps

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.

Provenance & Evidence