Réaction #3434

Équation de réaction

4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole

BBr3 CH2Cl2

→

4-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole

Rendement 49.0%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Concentrationconcentrated at reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
3. 3
   Lavagewashed with brine
4. 4
   Séchagedried (MgSO4)
5. 5
   ConcentrationAfter concentrating at reduced pressure
6. 6
   Autrethe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

Mode opératoire

A solution of 1.25 g (5 mmol) of 4-methoxy-2-methyl-1-(phenylmethyl)-1H-indole and 20 mL of 1M BBr3 /CH2Cl2 in 50 mL of methylene chloride was stirred at room temperature for 5 hours and concentrated at reduced pressure. The residue was dissolved in ethyl acetate, washed with brine and dried (MgSO4). After concentrating at reduced pressure, the residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 577 mg (49% yield) of 4-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole, 125°-127° C.

Source