Carbon tetrabromide → 1-benzhydryl-3-(2-bromoethyl)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indole

Participants

Reaction Conditions

Reaction Steps

A solution was made with 1 eq 2-[1-benzhydryl-2-({[tert -butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indol-3-yl]ethanol and CH2Cl2 (0.12M). Then 0.76 eq of 1,3-bis(diphenylphosphino)propane was added and the solution was cooled to 0° C. under N2. Then 1.3 eq of CBr4 was added to give a light yellow solution. The reaction was allowed to return to room temperature. After three hours and 15 minutes the solvent was removed. Purified using a flash column with silica gel and 1:5 EtOAc/Hexane as eluent to give 1-benzhydryl-3-(2-bromoethyl)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-chloro-1H-indole (yellow-brown gum) in 90% yield.

Provenance & Evidence