Carbon Dioxide → Methyl 5-cyano-2-methoxybenzoate

HRID 78526

Reaktionsgleichung

Reaktionsgleichung von HRID 78526
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]#[N:6].[CH2:12](N(CC)CC)C.[C:19](=[O:21])=[O:20]>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:12][O:20][C:19](=[O:21])[C:2]1[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Komponenten

6

Edukt 3

HCID 280Carbon DioxideHCID 8471TriethylamineHCID 7360493-Bromo-4-methoxybenzonitrile

Produkt 1

HCID 18464789Methyl 5-cyano-2-methoxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3-bromo-4-methoxybenzonitrile (Aldrich) (10.0 g, 47.2 mmol), PdCl2(dppf)-CH2Cl2 adduct (Aldrich) (1.00 g, 1.22 mmol) and triethylamine (12.5 mL, 89.7 mmol) in 100 mL of methanol in a high pressure vessel was heated to 100° C. at 60 psi of CO2 for 4 h. The mixture was cooled to room temperature and filtered. The mixture was concentrated under reduced pressure to afford the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 3.91 (s, 3H), 3.98 (s, 3H), 7.06 (d, J=8.5 Hz, 1H), 7.76 (dd, J=8.7, 2.3 Hz, 1H), 8.10 (d, J=2.1 Hz, 1H).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-006cd4b42e45497db65fe173f11d498f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841334B2

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