Diethyl disulfide → 6-ethylsulfanyl-1H-indole

Temperature

-78 °C

To a mixture of potassium hydride (30% wt. in mineral oil, 2.71 g, 20.2 mmol) and THF (30 mL) was added a solution of 6-bromoindole (3.98 g, 20.3 mmol) in THF (10 mL) at 0° C. After 15 minutes the solution was cooled to −78° C., and tert-butyllithium (1.5 M in pentane, 27.07 mL, 40.60 mmol) was added via syringe. The mixture was stirred at −78° C. for 10 min then ethyl disulfide (4.97 g, 40.6 mmol) in THF (10 mL) was added. The reaction mixture was allowed to warm to room temperature, poured into ice-sat.aq. NH4Cl (150 mL), and then extracted with EtOAc (150 mL). The organic phase was washed with water (150 mL), brine (150 mL), dried over Mg2SO4, concentrated, and purified on silica gel (EtOAc/hexane 5% to 15%), to provide 6-ethylsulfanyl-1H-indole (2.75 g, 77%) as a clear liquid.

1. temperatureto warm to room temperature
2. additionpoured into ice-sat.aq
3. extractionNH4Cl (150 mL), and then extracted with EtOAc (150 mL)
4. washThe organic phase was washed with water (150 mL), brine (150 mL)
5. dry with materialdried over Mg2SO4
6. concentrationconcentrated
7. custompurified on silica gel (EtOAc/hexane 5% to 15%)

ORD record

ord-d5eca2d8f5c040cc812ff35b9b9bc818

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772271B2