Iodine → HCID 58955089, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 4-bromo-1H-indole (4.69 g, 23.9 mmol) in ethanol (110 mL) was added thiophenol (2.46 mL, 23.9 mmol). A solution of potassium iodide (3.97 g, 24 mmol) and iodine (6.07 g, 24 mmol) dissolved in water (5 mL) and ethanol (5 mL) is added over 5 minutes and the reaction was heated at 45° C. for 12 hours. The brown reaction is concentrated in vacuo to a dark brown oil and diluted with ethyl acetate (250 mL). The organic layer is washed with water (80 mL×2), saturated Na2S2O3 (80 mL), and brine (80 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (20-30% ethyl acetate/petroleum ether) gave the title compound as a white solid (7.24 g, 99.5%). Mp: 137-139° C. MS (ES−): 302 (M−H).

Provenance & Evidence