Diethyl disulfide → 6-ethylsulfanyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence