Hydrochloric Acid → 3-Fluoro-4-(methylsulphonyl)benzeneboronic acid

HRID 732748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732748
[F:1][C:2]1[CH:3]=[C:4]([B:12]2[O:16]C(C)(C)C(C)(C)[O:13]2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].O1CCCC1.O.Cl>C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([B:12]([OH:16])[OH:13])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 593927762-(3-Fluoro-4-(methylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 459336283-Fluoro-4-(methylsulphonyl)benzeneboronic acidAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Combine 2-(3-fluoro-4-methanesulfonyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (222 mg, 0.74 mmol), NalO4 (474 mg, 2.2 mmol), tetrahydrofuran (THF, 4 mL) and water (1 mL). Stir for 2 hours and add 2M HCl in diethyl ether (0.2 mL). Stir another 12 hours and filter away the solid. Wash the filtrate with brine (10 mL), dry with MgSO4 and evaporate the solvent. Wash the solid with hexane (2×10 mL) and ether (10 mL). Dry the solid under vacuum to obtain 68 mg of the title compound (42%).

Aufarbeitung

  1. stirringStir another 12 hours
  2. filtrationfilter away the solid
  3. washWash the filtrate with brine (10 mL)
  4. dry with materialdry with MgSO4
  5. customevaporate the solvent
  6. washWash the solid with hexane (2×10 mL) and ether (10 mL)
  7. customDry the solid under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-20426403da7c49529fd3eb5555dc875c
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585977B2

Notizen zur Reaktion

Wird geladen…