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- W4213042816 abstract "[60839-94-3] C7H7FS (MW 142.21) InChI = 1S/C7H7FS/c8-6-9-7-4-2-1-3-5-7/h1-5H,6H2 InChIKey = ZDJQWFUQFDIBLS-UHFFFAOYSA-N (synthesis of α-fluoro substituted sulfoxides1 and sulfones1e,2) Physical Data: bp 60 °C/0.3 mmHg; nD22 1.5415. Solubility: sol CH2Cl2, CHCl3, MeOH. Preparative Methods: there are several methods of preparation. The reaction of Chloromethyl Phenyl Sulfide with Potassium Fluoride and 18‐Crown‐6 gives fluoromethyl phenyl sulfide in good yield (eq 1).1c Alternatively, the compound can be prepared by reaction of methyl phenyl sulfoxide with N,N‐Diethylaminosulfur Trifluoride (F3SNEt2, DAST) (eq 2),1d,2, 3 or with DAST and Antimony(III) Chloride (eq 3).1e,f,4 (1) (2) (3) Direct α-fluorination of methyl phenyl sulfides can be performed by using DAST, antimony(III) chloride (eq 4),1f N-fluoro-2,4,6-trimethylpyridinium triflate (eq 5),5 and Xenon(II) Fluoride.6 α-Fluorination of sulfides by an electrolytic process is also known. However, it has not been used widely in organic synthesis.7 (4) (5) Of the methods reported, the routes shown in eqs 1-4 are more often used synthetically. α-Monosubstituted fluoromethyl phenyl sulfides are prepared from the reaction of the corresponding thioacetals with Mercury(II) Fluoride (eq 6).8 (6) Handling, Storage, and Precautions: the compound should be used as soon as possible after purification by distillation. Storing it at 5 °C overnight then warming it to room temperature causes polymerization. Handle in a fume hood." @default.
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- W4213042816 date "2001-04-15" @default.
- W4213042816 modified "2023-09-26" @default.
- W4213042816 title "Fluoromethyl Phenyl Sulfide" @default.
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- W4213042816 doi "https://doi.org/10.1002/047084289x.rf008" @default.
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