Hydrochloric Acid → 4-Aminophenylsulphur pentafluoride

Temperature

80 °C

A solution of tin(II) chloride (1465 g., 7.73 mol) in concentrated (32 percent) aqueous HCl solution was heated with stirring to 80° C. and then, with ice cooling, 4-nitrophenylsulfur pentafluoride (584 g., 2.344 mol) was introduced in 8 portions over the course of 1 h. The internal temperature was kept below 100° C. during this. Subsequently, the mixture was stirred at an internal temperature of 85° C. for 1.5 h and then cooled to 45° C. over the course of a further hour. A mixture of ice (12 kg), NaOH (2 kg) and dichloromethane (1.5 l) was prepared and added to the reaction mixture with vigorous stirring. The phases were separated, the aqueous phase was extracted 3 times with 1 l of dichloromethane each time, and the combined organic phases were dried over Na2SO4 and evaporated in vacuo. 510 g (99%) of 4-aminophenylsulfur pentafluoride were obtained as a pale yellow crystalline powder, m.p. 63-65° C. (Bowden, R. D., Comina, P. J., Greenhall, M. P., Kariuki, B. M., Loveday, A., Philip, D. Tetrahedron 2000, 56, 3399: 57-59° C.).

1. temperaturewas heated
2. customwas kept below 100° C.
3. stirringSubsequently, the mixture was stirred at an internal temperature of 85° C. for 1.5 h
4. temperaturecooled to 45° C. over the course of a further hour
5. customwas prepared
6. additionadded to the reaction mixture with vigorous stirring
7. customThe phases were separated
8. extractionthe aqueous phase was extracted 3 times with 1 l of dichloromethane each time
9. dry with materialthe combined organic phases were dried over Na2SO4
10. customevaporated in vacuo

ORD record

ord-eabdba0a7fe94872afa49c970700bd00

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07659429B2