Réaction #2075738

Équation de réaction

PBr3

tert-butyl 4-(hydroxymethyl) 1H-1-indolecarboxylate

N-Boc-4-hydroxymethyl indole

NaHCO3

→

tert-butyl 4-(bromomethyl)-1H-1-indolecarboxylate

Rendement 84.0%

Solvants

ether

CH2Cl2

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONafter the addition
2. 2
   Extractionextracted with ethyl acetate (3×80 mL)
3. 3
   ExtractionThe combined extract
4. 4
   Lavagewas washed sequentially with water (80 mL), and brine (80 mL)
5. 5
   Séchagedried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationfinally concentrated

Mode opératoire

PBr3 (2.4 mL. 25.8 mmol) was added dropwise at 0° C. under nitrogen to a stirred solution of tert-butyl 4-(hydroxymethyl) 1H-1-indolecarboxylate 6 (6.0 g, 24.3 mmol) in ether (80 mL) and CH2Cl2 (20 mL) under nitrogen. The reaction was completed 30 minutes after the addition. The mixture was poured into a cold aqueous NaHCO3 solution (100 mL) and extracted with ethyl acetate (3×80 mL). The combined extract was washed sequentially with water (80 mL), and brine (80 mL), then dried (MgSO4), filtered, and finally concentrated to provide tert-butyl 4-(bromomethyl)-1H-1-indolecarboxylate 7 (6.3 g, 84%) as an oil which was immediately taken to the next step.

Source