Iodine → 2-Iodobenzothiophene

Participants

Reaction Conditions

Reaction Steps

Butyllithium 1.6M in hexane (112.5 ml, 180 mmole) and absolute ether (70 ml) were placed in a 500 ml three-necked flask under an argon atmosphere and cooled in an ice bath to 0° C. Benzothiophene (20.1 g, 150 mmole) dissolved in absolute ether (40 ml) was then added dropwise within 30 minutes while cooling with ice and the mixture was stirred for 2.5 hours in an ice bath. The reaction mixture was left overnight in a cold cabinet. Iodine (75.0 g) and absolute ether (50 ml) were placed in a 500 ml capacity 3-necked flask under an argon atmosphere and the solution of the lithium compound was added dropwise while cooling with ice. The reaction mixture was slowly heated to room temperature, hydrolysed with water, washed with sodium thiosulfate solution and the organic phase was dried over sodium sulfate. The reaction solution was then concentrated by evaporation in vacuo and purified by means of flash chromatography with cyclohexane.

Provenance & Evidence