Carbon tetrabromide → 3-(2-bromoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole

Participants

Reaction Steps

3-(2-bromoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole was prepared according to method D Step III with 2-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol (1.44 g; 4.45 mmol) in THF (6 mL) and triphenyl phosphine (1.75 g; 6.67 mmol) and perbromomethane (2.21 g; 6.67 mmol) in THF (40 mL) pre-stirred for 30 minutes. The crude mixture was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 0.725 g (42%) of 3-(2-bromoethyl)-6-chloro-5-methyl-2-(triethylsilyl)-1H-indole as a brown oil.

Provenance & Evidence