Hydrochloric Acid → {4-[(Trifluoromethyl)sulfanyl]phenyl}boronic acid

HRID 1400008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400008
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([S:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[O:3]1.I([O-])(=O)(=O)=O.[Na+].Cl>C1COCC1.O>[F:19][C:16]([S:15][C:12]1[CH:11]=[CH:10][C:9]([B:4]([OH:5])[OH:3])=[CH:14][CH:13]=1)([F:18])[F:17]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 451588394,4,5,5-Tetramethyl-2-{4-[(trifluoromethyl)sulfanyl]phenyl}-1,3,2-dioxaborolane

Produkt 1

HCID 46739571{4-[(Trifluoromethyl)sulfanyl]phenyl}boronic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a round-bottomed flask was added 4,4,5,5-tetramethyl-2-(4-trifluoromethylsulfanyl-phenyl)-[1,3,2]dioxaborolane (960 mg, 3.16 mmol) and sodium periodate (2.03 g, 9.48 mmol) in THF and water (4:1, 26 mL). The resulting suspension was stirred at rt for 30 min. HCl (1 N aq., 2.21 mL) was added to the suspension and the reaction mixture was stirred at rt for 18 h. The resulting precipitate was removed by filtration and washed with hexanes. The filtrate was diluted with water (25 mL) and extracted with EtOAc (25 mL). The aqueous layer was extracted with EtOAc (10 mL×2), and the combined organic layers dried (Na2SO4) and concentrated to yield the title compound (512 mg, 73%).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at rt for 18 h
  2. customThe resulting precipitate was removed by filtration
  3. washwashed with hexanes
  4. additionThe filtrate was diluted with water (25 mL)
  5. extractionextracted with EtOAc (25 mL)
  6. extractionThe aqueous layer was extracted with EtOAc (10 mL×2)
  7. dry with materialthe combined organic layers dried (Na2SO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bf24e822bb864843bbf98dc2b1c0afa0
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906914B2

Notizen zur Reaktion

Wird geladen…