StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1423409
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1423409
Br[C:2]1[CH:7]=[C:6]([CH:8]([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[O:11][CH2:12][CH:13]1[CH2:15][CH2:14]1.[Li]CCCC.C(O[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1)(C)C>C(OC)CCC>[CH:13]1([CH2:12][O:11][C:3]2[CH:4]=[CH:5][C:6]([CH:8]([F:10])[F:9])=[CH:7][C:2]=2[B:25]2[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]2)[CH2:15][CH2:14]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 670330122-Bromo-1-(cyclopropylmethoxy)-4-(difluoromethyl)benzeneHCID 178418339Butyllithium

Produkt 1

HCID 670331782-[2-(Cyclopropylmethoxy)-5-(difluoromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12338
Butyl methyl ether
Lösungsmittel

Versuchsvorschrift

2-Bromo-1-cyclopropylmethoxy-4-difluoromethyl-benzene (example B.b18; 24.35 g; 87.9 mmol) is dissolved in dry tert. BuOMe (440 mL). n-BuLi (1.6M in hexane; 60.0 mL; 96.0 mmol) is slowly syringed into the well stirred reaction mixture at −40° C. After one hour commercially available 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (17.86 g; 96.0 mmol) is added at −40° C. followed by stirring at 0° C. for one additional hour. The reaction mixture is quenched by addition of 2M aqueous citric acid (90.0 mL). The organic layer is separated, washed with brine, dried over Mg2SO4 and filtered through a pad of neutral alumina (act.2-3). The solvent is removed under reduced pressure to yield 28.1 g of the title compound as pale yellow oil.

Aufarbeitung

  1. customreaction mixture at −40° C
  2. stirringby stirring at 0° C. for one additional hour
  3. customThe reaction mixture is quenched by addition of 2M aqueous citric acid (90.0 mL)
  4. customThe organic layer is separated
  5. washwashed with brine
  6. dry with materialdried over Mg2SO4
  7. filtrationfiltered through a pad of neutral alumina (act.2-3)
  8. customThe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-83874bd30c7e424d9f64c57fe1b14c54
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08927557B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion