Hydrogen Bromide → HCID 58137421, compound

3-Amino-5-(pentafluorosulfanyl)benzoic acid (1.1 g; example 2a) was dissolved in 24% hydrogen bromide solution (40 ml). While stirring and cooling, sodium nitrite solution (290 mg dissolved in 20 ml of water) was added dropwise, in the course of which the temperature was not to exceed 5° C. On completion of formation of the diazonium salt, copper(I) bromide solution (720 mg dissolved in 15 ml of 48% hydrobromic acid) was cooled to 0° C. while stirring and the above diazonium salt solution was slowly added dropwise. Then the cooling bath was removed and the mixture was stirred at RT for 3 h. Thereafter, the reaction mixture was diluted with water and extracted repeatedly with EA. The combined EA phases were dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in 500 ml of EA and filtered through a glass frit filled with a 10 cm silica gel layer. The filter layer was washed thoroughly with EA. The clear filtrate was concentrated, and solvent residues were drawn off under high vacuum. 800 mg of the title compound were obtained.

1. temperaturecooling
2. customto exceed 5° C
3. stirringwhile stirring
4. customThen the cooling bath was removed
5. stirringthe mixture was stirred at RT for 3 h
6. additionThereafter, the reaction mixture was diluted with water
7. extractionextracted repeatedly with EA
8. dry with materialThe combined EA phases were dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. dissolutionThe residue was dissolved in 500 ml of EA
12. filtrationfiltered through a glass frit
13. additionfilled with a 10 cm silica gel layer
14. washThe filter layer was washed thoroughly with EA
15. concentrationThe clear filtrate was concentrated

ORD record

ord-ab184da08c42426598bff0dfa44a30a9

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466169B2