Hydrochloric Acid → 2-(3-Methoxyphenyl)pyridine

HRID 16043

Reaktionsgleichung

Reaktionsgleichung von HRID 16043
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][CH:8]=1.BrC1C=C(OC)C=CC=1.[Mg].Br[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:6]=[CH:7][CH:8]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 79732-BromopyridineHCID 169713-BromoanisoleHCID 5462224MagnesiumHCID 178490745HCID 178490745, Verbindung

Produkt 1

HCID 27597152-(3-Methoxyphenyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

That is, as shown in the reaction scheme below, (3-methoxyphenyl)magnesium bromide was synthesized from 22.4 g (120 mmol) of 3-bromoanisole with 3.4 g of magnesium in dry tetrahydrofuran (THF) in an argon stream by a conventional manner. This was slowly added to a dry THF solution of 15.8 g (100 mmol) of 2-bromopyridine and 1.8 g of (1,2-bis(diphenylphosphino)ethane)dichloronickel (II) (Ni(dppe)Cl2) and the mixture was stirred at 50° C. for 1 hour. After adding 250 ml of 5% hydrochloric acid aqueous solution to the reaction mixture, the reaction mixture was extracted with chloroform to obtain a target substance and the organic layer was distilled under reduced pressure. 17.4 g (93.9 mmol) of 2-(3-methoxyphenyl)pyridine (3-MeO-PPy) was obtained as a colorless transparent liquid. Identification was performed by CHN elementary analysis and 1H-NMR.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with chloroform
  2. customto obtain a target substance
  3. distillationthe organic layer was distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d624a49d6a8146cdbb6f70d6ad12a919
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07736757B2

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