Triisopropyl borate → (2-Phenylthiophen-3-yl)boronic acid

HRID 1805492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1805492
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[B:13](OC(C)C)([O:18]C(C)C)[O:14]C(C)C.[Li]CCCC>C1COCC1.Cl>[C:7]1([C:3]2[S:4][CH:5]=[CH:6][C:2]=2[B:13]([OH:18])[OH:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 3

HCID 21531Triisopropyl borateHCID 114818273-Bromo-2-phenylthiopheneHCID 178418339Butyllithium

Produkt 1

HCID 57573251(2-Phenylthiophen-3-yl)boronic acidAusbeute 5,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of 3-bromo-2-phenylthiophene (1.99 g, 8.32 mmol) and B(Oi-Pr)3 (1.81 mL, 12.5 mmol) in THF (20 mL) was added n-BuLi (1.65 M in hexane, 10.1 mL, 16.6 mmol) at −78° C. The mixture was stirred at −78° C. for 30 min and at 0° C. for 30 min. The mixture was diluted with 1 M HCl aqueous solution at 0° C., extracted with EtOAc, washed with brine, dried over Na2SO4, filtered, concentrated in vacuo and purified by column chromatography on silica gel (hexane/EtOAc=90/10 to 0/100) to yield the title compound (87.4 mg, 5% yield) as a white solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 7.19 (1H, d, J=4.9 Hz), 7.27-7.44 (3H, m), 7.46-7.58 (3H, m), 8.06 (2H, s).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography on silica gel (hexane/EtOAc=90/10 to 0/100)

Quellen und Nachweise

ORD-Eintrag
ord-9ed85f64e1c144ea8e736d48219c8a67
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354411B2

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