Synthesis
Methylene ditosylate (100 mg, 0.28 mmol) and caesium fluoride (213 mg, 1.4 mmol) were dissolved in tert-amyl alcohol (5 mL) and irradiated in a microwave for 15 minutes at 90 °C. The reaction was allowed to cool and the tert-amyl alcohol was removed under reduced pressure, ice-cold diethyl ether was added and the suspension filtered, and then washed with plenty of ice-cold diethyl ether. The filtrate was concentrated under reduced pressure to yield Fluoromethyl 4-Methylbenzenesulfonate as a colourless oil (49 mg, 88% yield).
References
[1] Tetrahedron Letters, 2018, vol. 59, # 17, p. 1635 - 1637
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 18, p. 3956 - 3960
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2003, vol. 46, # 6, p. 555 - 566
[4] ChemMedChem, 2016, vol. 11, # 1, p. 108 - 118
[5] Patent: WO2012/40133, 2012, A2. Location in patent: Page/Page column 36-37
