Pentane → 3-bromo-1-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-1H-indole

Participants

Reaction Conditions

Reaction Steps

A 1.6 M solution of BuLi in pentane (30.7 ml, 49.2 mmol) was added to a solution of 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole (9.36 g, 37.8 mmol) in THF (190 ml) at −78° C. within 20 min under an argon atmosphere. The reaction mixture was stirred for 20 min at −78° C. tert-Butyldimethylsilyl chloride (7.64 g, 49.2 mmol) was added and the reaction mixture was stirred for 10 min at −78° C. and for 1 h at RT. The mixture was chilled to −78° C., N-bromosuccinimide (7.64 g, 41.6 mmol) was added and the solution was stirred for 1 h at −78° C. and for 1 h at RT. Diethyl ether was added and the mixture was washed with saturated aqueous NaHCO3 solution and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, CH2Cl2/heptane 1:19) to give 12.87 g (29.2 mmol, 77%) 3-bromo-1-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-1H-indole.

Provenance & Evidence