Reaktion #160765

Reaktionsgleichung

4-(5-methylcyclohexa-1,3-dienyl)-3-nitropyridine

NBS

ethyl acetate

→

(+/−)-6-bromo-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol

Ausbeute 80.0%

Lösungsmittel

THF

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Trocknenthe organic phase was dried with brine
2. 2
   Filtrationsodium sulfate, filtered
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe crude material was purified via silica gel column chromatography
5. 5
   Wascheneluting with ethyl acetate and hexanes (1:1)

Vorschrift

To a solution of 4-(5-methylcyclohexa-1,3-dienyl)-3-nitropyridine (1.0 equiv.) in THF and water (1:1, 0.13M) was added NBS (1.5 equiv.) and the reaction was stirred at room temperature for 30 min. Upon completion, ethyl acetate and water were added to the reaction, the organic phase was dried with brine, then sodium sulfate, filtered, and concentrated. The crude material was purified via silica gel column chromatography eluting with ethyl acetate and hexanes (1:1) to give (+/−)-6-bromo-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol as a yellow oil in 80% yield. LC/MS=315.0/313.0 (M+H), LC=2.966 min.

Quelle