Dichloromethane → HCID 15965625, compound

Temperature

70 °C

A mixture of Cs2CO3 (794 g, 2.7 mol), dimethoxyethane (2 l), water (300 ml) and trimethylboroxine (50 percent solution in THF, 225 g, 0.9 mol) was heated to 70° C., PdCl2 (dppf).CH2Cl2 (37 g, 45 mmol) was added, and a solution of 4-amino-3-bromophenyl sulfur pentafluoride (270 g, 0.9 mol) in dimethoxyethane (400 ml) was added dropwise within 2 h while the reaction mixture was heated to reflux. It was subsequently heated to reflux for a further 3 h and then cooled to room temperature, diluted with MTB (500 ml), filtered through a silica gel column (14×7 cm, 70-200 μm) and washed with MTB (2500 ml). The filtrate was concentrated under reduced pressure. 490 g of a black, semicrystalline mass were obtained and were subjected to a steam distillation. A total of 5.5 l of condensate was collected, from which the crystals of the product separated out. The condensate was extracted 3 times with MTB, and the combined organic phases were dried over Na2SO4 and concentrated under reduced pressure. 4-Amino-3-methylphenylsulfur pentafluoride (181 g, 76%) was obtained as colorless crystals, m.p. 65-66° C.

1. temperaturewas heated to reflux
2. temperatureIt was subsequently heated
3. temperatureto reflux for a further 3 h
4. temperaturecooled to room temperature
5. additiondiluted with MTB (500 ml)
6. filtrationfiltered through a silica gel column (14×7 cm, 70-200 μm)
7. washwashed with MTB (2500 ml)
8. concentrationThe filtrate was concentrated under reduced pressure
9. custom490 g of a black, semicrystalline mass were obtained
10. distillationwere subjected to a steam distillation
11. customA total of 5.5 l of condensate was collected, from which the crystals of the product
12. customseparated out
13. extractionThe condensate was extracted 3 times with MTB
14. dry with materialthe combined organic phases were dried over Na2SO4
15. concentrationconcentrated under reduced pressure

ORD record

ord-9dabfd3c2ae54a2b8ec22318031fd1a9

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07317124B2