Triisopropyl borate → (5,6,7,8-Tetrahydro-5,5-dimethylnaphth-2-yl)boronic acid

HRID 24575

Reaktionsgleichung

Reaktionsgleichung von HRID 24575
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6][CH2:5]2.[Li]CCCC.C([O:22][B:23](OC(C)C)[O:24]C(C)C)(C)C>C1(C)C=CC=CC=1.Cl>[CH3:12][C:8]1([CH3:13])[CH2:7][CH2:6][CH2:5][C:4]2[CH:3]=[C:2]([B:23]([OH:24])[OH:22])[CH:11]=[CH:10][C:9]1=2

Komponenten

6

Edukt 3

HCID 21531Triisopropyl borateHCID 105860636-Bromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

Produkt 1

HCID 22571498(5,6,7,8-Tetrahydro-5,5-dimethylnaphth-2-yl)boronic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a cold (−78° C.) solution of 2.02 g (8.4 mmol) of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene in 11.0 mL of toluene, was added 4.6 g (6.8 mL, 10.9 mmol, 1.6 M in hexane) of n-BuLi. The resulting solution was stirred at −78° C. for 45 min. and then 2.40 g (3.0 mL, 12.7 mmol) of triisopropylborate was dropwise added and the reaction stirred at room temperature for 12 h. The reaction was then diluted with 10% HCl, and extracted with ether (2×). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give an oil. Recrystallization from hexane afforded the title compound as a white solid.

Aufarbeitung

  1. stirringthe reaction stirred at room temperature for 12 h
  2. extractionextracted with ether (2×)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customRecrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-1d3460c5657a46a1b80f064616bcbac3
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855832B2

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