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-bromophenylsulfur pentafluoride (270 g, 0.9 mol) in dimethoxyethane (400 ml) was added dropwise over the course of 2 h while the reaction mixture was heated to reflux. It was subsequently heated under reflux for a further 3 h and then cooled to room temperature, diluted with MTB ether (500 ml), filtered through a silica gel column (14×7 cm, 70-200 μm) and washed with MTB ether (2500 ml). The filtrate was evaporated in vacuo. 490 g of a black, semicrystalline mass was obtained and was 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× with MTB ether, and the combined organic phases were dried over Na2SO4 and evaporated in vacuo. 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. temperatureunder reflux for a further 3 h
4. temperaturecooled to room temperature
5. filtrationfiltered through a silica gel column (14×7 cm, 70-200 μm)
6. washwashed with MTB ether (2500 ml)
7. customThe filtrate was evaporated in vacuo
8. custom490 g of a black, semicrystalline mass was obtained
9. distillationwas subjected to a steam distillation
10. customA total of 5.5 l of condensate was collected, from which the crystals of the product
11. customseparated out
12. extractionThe condensate was extracted 3× with MTB ether
13. dry with materialthe combined organic phases were dried over Na2SO4
14. customevaporated in vacuo

ORD record

ord-83012776020d417e8a3defa4820d1f2e

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622611B2