2-Chloroaniline → 7-Chloro-2-methyl-3-methylsulfanyl-1H-indole

Temperature

-65 °C

Using the procedure described in J. Amer. Chem. Soc., 1974, 96 (17) 5495 , 2-chloroaniline (1.27 g, 10 mmole) was dissolved in dichloromethane (35 ml) and cooled to −65° C. To this solution was added dropwise with vigorous stirring, t-butyl hypochlorite (1.08 g, 10 mmole) in dichloromethane (5 ml). After 10 minutes 1-methylsulfanyl-propan-2-one (1.04 g, 10 mmole) dissolved in dichloromethane (5 ml) was added. The mixture was stirred at −65° C. for 1 h more. At this point triethylamine (1.01 g, 10 mmole) dissolved in dichloromethane (5 ml) was added. Upon completion of the addition, the reaction mixture was allowed to reach ambient temperature. Water was added and the layers were separated, the organic layer was dried over magnesium sulfate, filtered and the solvent evaporated to dryness. The residue was purified by column chromatography on silica gel using a mixture of hexane-ethyl acetate (95:5) to elute 7-chloro-2-methyl-3-methylsulfanyl-1H-indole (1.94 g) as an oil.

1. additionwas added
2. additionwas added
3. additionUpon completion of the addition
4. customto reach ambient temperature
5. customthe layers were separated
6. dry with materialthe organic layer was dried over magnesium sulfate
7. filtrationfiltered
8. customthe solvent evaporated to dryness
9. customThe residue was purified by column chromatography on silica gel using
10. additiona mixture of hexane-ethyl acetate (95:5)
11. washto elute 7-chloro-2-methyl-3-methylsulfanyl-1H-indole (1.94 g) as an oil

ORD record

ord-b4f5cb2c432f42aeafa008ca074bfba8

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06852726B2