Cesium fluoride → (Fluoromethyl)(p-tolyl)sulfane

Cesium fluoride (149.55 g, 2 eq) was added to a mixture of PEG400 (90 mL) and acetonitrile (540 mL). The mixture was stirred a few minute under an argon atmosphere and then acetonitrile (90 mL) was removed by distillation. (Chloromethyl)(p-tolyl)sulfane (102.68 g, 492.25 mmol) was added. The reaction mixture was stirred at a temperature between 80° C. and 85° C. until the reaction was complete. The suspension formed, was filtered and the filtrate was concentrated. The crude product was purified by distillation to give 52.09 g (68%) of the desired product as slightly yellow oil (bp: 57° C. at 40 Pa).

1. customacetonitrile (90 mL) was removed by distillation
2. stirringThe reaction mixture was stirred at a temperature between 80° C. and 85° C. until the reaction
3. customThe suspension formed
4. filtrationwas filtered
5. concentrationthe filtrate was concentrated
6. distillationThe crude product was purified by distillation

ORD record

ord-8c94c35ed9bc46bf85ee5c7e87790d63

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290446B2