1,2-Dimethoxyethane → 2-(Biphenyl-3-yl)-4-tert-butylpyridine

HRID 1910354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910354
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[C:12]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1.C([O-])([O-])=O.[K+].[K+].COCCOC>O>[C:12]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:17]=[CH:16][CH:15]=[C:14]([C:2]2[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][N:3]=2)[CH:13]=1

Komponenten

6

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 2734315(3-Phenylphenyl)boronic acidHCID 131833052-Bromo-4-tert-butylpyridine

Produkt 1

HCID 593439852-(Biphenyl-3-yl)-4-tert-butylpyridineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

15.0 g (0.7 mol) of 2-bromo-4-tert-butyl-pyridine was added to 13.8 g (0.7 mol) of 3-biphenylboronic acid, 2.4 g (0.002 mol) of Pd(Ph3)4, 26 g (0.188 mol) of K2CO3, 100 mL of DME and 100 mL of water. The reaction mixture was refluxed for 20 hours and separated on silica gel column with 10% ethyl acetate in hexane. ˜18.0 g (˜90% yield) 2-(biphenyl-3-yl)-4-tert-butylpyridine was obtained. MS confirmed the desired product.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 20 hours
  2. customseparated on silica gel column with 10% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-a1af5b6d20e747c5b01f30c0c11f2b47
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08603645B2

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