α,α-Difluorotoluene and sulfinyl fluoride could be produced through the following synthetic routes.

Phenylsulfur trifluoride2 (16.6 g., 0.10 mole) is placed in a two-necked 50-ml. flask equipped with a dropping funnel and connected to a dry distillation column. The flask is heated to 50–70° in an oil bath, and 10.6 g. (0.10 mole) of benzaldehyde is added in small portions over 30 minutes. A mild exothermic reaction occurs. After the addition is completed, the reaction flask is heated to 100° with an oil bath, and the pressure on the column is reduced until α,α-difluorotoluene distills. The major portion of product distills at 68° (80 mm.), but a small final cut, b.p. 45° (15 mm.), is obtained. The yield of α,α-difluorotoluene is 9.2–10.2 g. (71–80%). The pressure is reduced and the distillation is continued. An intermediate cut of 1–2 g., b.p. 45° (15 mm.) to 60° (2.5 mm.), is discarded, and benzenesulfinyl fluoride, 11.7–13.2 g. (81–91%), b.p. 60° (2.5 mm.), is collected. Since the benzenesulfinyl fluoride slowly attacks glass and may be unstable to storage at room temperature, it is recommended that this product be stored at -80°.

Notice: Phenylsulfur trifluoride is toxic, and this reaction should be carried out in a good hood. The reagent should not be allowed to come in contact with the skin.