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2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 4,4,5,5-Tetramethyl-2-(4-octylphenyl)-1,3,2-dioxaborolane

HRID 601456
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 601456
[Li]CCCC.I[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=1.C(O[B:25]1[O:29][C:28]([CH3:31])([CH3:30])[C:27]([CH3:33])([CH3:32])[O:26]1)(C)C>C1COCC1>[CH3:32][C:27]1([CH3:33])[C:28]([CH3:31])([CH3:30])[O:29][B:25]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=2)[O:26]1
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Komponenten

5

Edukt 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 115948361-Iodo-4-octylbenzeneHCID 178418339Butyllithium

Produkt 1

HCID 588233864,4,5,5-Tetramethyl-2-(4-octylphenyl)-1,3,2-dioxaborolane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

n-BuLi (16.6 mL, 1.6 M in hexanes) was added over 10 minutes to a solution of 1-iodo-4-octylbenzene from Part A (6.9 g, 21.8 mmol) in dry THF (100 mL) at −78° C. under a nitrogen atmosphere. The mixture was stirred for another 10 minutes at −78° C. 2-Isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (6.21 mL, 30.4 mmol) was subsequently added dropwise to the mixture and stirring was continued at room temperature overnight. The reaction was then quenched with distilled water, and THF was removed under vacuum. The product was then extracted into diethyl ether and the organic layer was washed with brine, dried over MgSO4, filtered and evaporated in vacuo to give 6.38 g of 4,4,5,5-tetramethyl-2-(4-octylphenyl)-1,3,2-dioxaborolane as a colorless oil. The product was used in the next step without further purification.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued at room temperature overnight
  3. customThe reaction was then quenched with distilled water, and THF
  4. customwas removed under vacuum
  5. extractionThe product was then extracted into diethyl ether
  6. washthe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e2477bd9e1ec49968840cad319376436
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07902363B2

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