Reaktion #45623

Reaktionsgleichung

2-Cyclopropyl-6-[1-(ethoxy)ethenyl]-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile

water

N-bromosuccinimide

→

compound

Ausbeute 81.2%

6-(2-Bromoacetyl)-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile

Ausbeute 81.2%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter the reaction
2. 2
   Sonstigethe solvent was evaporated away under reduced pressure
3. 3
   Waschenby washing with water and saturated brine
4. 4
   TrocknenThe obtained organic layer was dried over anhydrous sodium sulfate
5. 5
   Sonstigethe solvent was evaporated away under reduced pressure
6. 6
   Wascheneluted with a mixed solvent of n-hexane/ethyl acetate (2:1

Vorschrift

2-Cyclopropyl-6-[1-(ethoxy)ethenyl]-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile (I-84) (2.58 g, 8.46 mmol) was dissolved in tetrahydrofuran (130 ml), water (7.7 ml) and N-bromosuccinimide (1.61 g, 8.89 mmol) were added all at a time, followed by stirring at room temperature for 1.5 hours. After the reaction, the solvent was evaporated away under reduced pressure, followed by dilution with ethyl acetate and by washing with water and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography (covering) and eluted with a mixed solvent of n-hexane/ethyl acetate (2:1, v/v) to obtain the entitled compound (2.40 g, 81%) as a yellow white solid.

Quelle