Réaction #2045461

Équation de réaction

3,6-dibromo-9-H-carbazole

CMMP

→

title compound

Rendement 60.0%

(±)-3,6-Dibromo-9-(oxiran-2-ylmethyl)carbazole

Rendement 60.0%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   workup.ADDITION1996, 37(14), 2459-2462) (0.20 g, 1.74 mmol) is added
2. 2
   AutreThe solvent is evaporated
3. 3
   Autrethe crude compound is purified via flash chromatography

Mode opératoire

At rt under an inert atmosphere, (±)-glycydol (0.129 g, 1.74 mmol, 120 uL) is added into a solution of 3,6-dibromo-9-H-carbazole (0.565 g, 1.74 mmol) in anhydrous toluene (10 mL). Then CMMP (which is prepared according to the protocol of Tetsuto, Tsunoda Tett. Lett. 1996, 37(14), 2459-2462) (0.20 g, 1.74 mmol) is added. The resulting mixture is allowed to stir at rt for 16 hours. The solvent is evaporated and the crude compound is purified via flash chromatography using Biotage device and Petroleum Ether/DCM (3/1) as eluant to give the title compound in a 60% yield as a white solid and 5% of (±)-3,6-dibromo-9-[(1E)-3-(3,6-dibromocarabazol-9-yl)propen-1-enyl]carbazole as a grey powder.

Source