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

Hydrochloric Acid → 4'-Pentyl-4-biphenylboronic Acid (contains varying amounts of Anhydride)

HRID 2369636
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2369636
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.II.[B:21](OC)([O:24]C)[O:22]C.Cl>C1COCC1>[CH2:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([B:21]([OH:24])[OH:22])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH2:15][CH2:16][CH2:17][CH3:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 8470Trimethyl borateHCID 6187094-Bromo-4'-pentylbiphenyl

Produkt 1

HCID 154580894'-Pentyl-4-biphenylboronic Acid (contains varying amounts of Anhydride)Ausbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

4-Bromo-4′-pentylbiphenyl (3 g, 9.9 mmol) was added in one portion to Mg (0.27 g, 11.1 mmol), treated with I2, in THF (40 mL). The mixture was heated at reflux for 3 h, cooled to −78° C. and trimethyl borate (2.06 g, 19.8 mmol) was added dropwise. The mixture was warmed to room temperature over 1 h, acidified with HCl (2 M, 50 mL), extracted with Et2O (3×50 mL). The combined ethereal washes were extracted with NaOH (100 mL, 1 M). The aqueous phase was acidified with concentrated HCl, extracted with Et2O (3×50 mL), dried (MgSO4) and the solvent removed under reduced to give the title compound (2.07 g, 78%) as an off white powder.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. temperatureThe mixture was warmed to room temperature over 1 h
  4. extractionextracted with Et2O (3×50 mL)
  5. extractionThe combined ethereal washes were extracted with NaOH (100 mL, 1 M)
  6. extractionextracted with Et2O (3×50 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-35e97ac7a0a546958f8063dea8c81ab0
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08703978B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion