Carbon tetrabromide → 4-(2,2-Dibromovinyl)-5,7-dimethyl-1-tosyl-1H-indole

Participants

Reaction Steps

To a solution of 5,7-dimethyl-1-tosyl-1H-indole-4-carbaldehyde (Example 46-D) (1.5 g, 4.58 mmol) and CBr4 (3.04 g, 9.16 mmol) in CH2Cl2 (50 mL) was added PPh3 (3.61 g, 13.74 mmol) at 0° C., and then the mixture was stirred at room temperature for 1 hr. The reaction mixture was directly purified by silica gel flash chromatography (heptanes/EtOAc=1/0 to 1/1) to give the title compound. MS (ESI+) m/z 483.9, 485.9, 481.9, 487.1 (M+H).

Provenance & Evidence