Reaction #8427

Reaction equation

4-bromoindole

o-methylbenzenesulfonyl chloride

→

title compound

Yield 87.0%

4-Bromo-1-(2-methyl-benzenesulfonyl)-1H-indole

Yield 87.0%

Conditions

Workup

1. 1
   workup.ADDITIONa 9:1 mixture of ortho and para methyl isomers) (1.29 g, 6.78 mmol)
2. 2
   OtherPurification by column chromatography (SiO2, CH2Cl2:heptane)

Procedure

The compound was prepared from 4-bromoindole (1.02 g, 5.25 mmol) and o-methylbenzenesulfonyl chloride (a 9:1 mixture of ortho and para methyl isomers) (1.29 g, 6.78 mmol) according to method 4. Purification by column chromatography (SiO2, CH2Cl2:heptane) gave 1.6 g (87%) of the title compound which contains ca 10% of the p-methyl isomer) as a light purple viscous oil: 1H NMR (CD3OD) δ 7.94–6.68 (m, 9H), 2.52 (s, 3H); MS (ESI) 352.3 (M+H)+; Purity (HPLC) >95%.

Source