Dichloromethane → 3-Methyl-5-nitro-2-phenylpyridine

HRID 41978

Reaktionsgleichung

Reaktionsgleichung von HRID 41978
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O>[CH3:8][C:7]1[C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:3][CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 52004662-Bromo-3-methyl-5-nitropyridine

Produkt 1

HCID 463150573-Methyl-5-nitro-2-phenylpyridineAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

In a schlenck tube, a mixture of 2-bromo-3-methyl-5-nitropyridine (4.6 mmol, 1.0 g), phenylboronic acid (4.6 mmol, 0.560 g), PdCl2dppf.DCM (0.47 mmol, 0.4 g), Cs2CO3 (13.8 mmol, 4.5 g) in a dioxane/water 4:1 mixture (18 ml) was heated at 100° C. for 14 hours, under argon atmosphere. The solvent was evaporated and the crude mixture was extracted between water and ethyl acetate. The solid residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate mixtures affording 3-methyl-5-nitro-2-phenylpyridine (0.95 g, yield 97%) as major product.

Aufarbeitung

  1. customThe solvent was evaporated
  2. extractionthe crude mixture was extracted between water and ethyl acetate
  3. customThe solid residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-6712a36184ac4dfaa445b8e584cf2b21
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536165B2

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