1-Bromopropane → 2-(3,5-Dimethyl-4-propoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1690675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690675
[CH3:1][C:2]1[CH:7]=[C:6]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)[CH:5]=[C:4]([CH3:17])[C:3]=1[OH:18].Br[CH2:20][CH2:21][CH3:22].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:17][C:4]1[CH:5]=[C:6]([B:8]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH3:16])([CH3:15])[O:9]2)[CH:7]=[C:2]([CH3:1])[C:3]=1[O:18][CH2:20][CH2:21][CH3:22]

Komponenten

5

Edukt 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 27346492,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Produkt 1

HCID 576184902-(3,5-Dimethyl-4-propoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture 2,6-Dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (500 mg, 2.02 mmol, 1 eq.), 1-bromopropane (793 mg, 6.45 mmol, 3.2 eq.), and K2CO3 (334 mg, 2.42 mmol, 1.2 eq.) in acetone (20 mL) is heated at 65° C. for 4 days. After cooling to room temperature, the reaction is concentrated, diluted with EtOAc and sequentially washed with H2O and saturated aqueous NaCl. The organic solution is dried over Na2SO4 and concentrated to give 2-(3,5-Dimethyl-4-propoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane as a clear oil.

Aufarbeitung

  1. concentrationthe reaction is concentrated
  2. additiondiluted with EtOAc
  3. washsequentially washed with H2O and saturated aqueous NaCl
  4. dry with materialThe organic solution is dried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2d6f8e605e434f208aef6342a71d9c6a
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153671B2

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