Hydrochloric Acid → 3-Hydroxy-5-(pentafluorosulfanyl)benzoic acid

Temperature

100 °C

2.0 g (6.11 mmol) of the compound of Example 15A were dissolved in 20 ml of dioxane and 2 ml of water, the mixture was degassed with argon, 280 mg (0.31 mmol) of tris(dibenzylideneacetone)dipalladium, 325 mg (0.76 mmol) of 2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl and 1.37 g (24.5 mmol) of powdered potassium hydroxide were added and the mixture was stirred at 100° C. for 2 h. The reaction was then stirred into 50 ml of 1 M hydrochloric acid and extracted twice with in each case 50 ml of ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. The residue was suspended in dichloromethane/pentane (9:1), the solid was filtered off and the filter cake was dried under high vacuum. This gave 980 mg (59% of theory) of the title compound.

1. additionwere added
2. extractionextracted twice with in each case 50 ml of ethyl acetate
3. washThe combined organic phases were washed with saturated sodium chloride solution
4. dry with materialdried over sodium sulphate
5. concentrationconcentrated under reduced pressure
6. filtrationthe solid was filtered off
7. customthe filter cake was dried under high vacuum

ORD record

ord-2b287bdb33f7402dbf5e971fb5567daa

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394309B2