Iodine → 2-Iodobenzothiophene

Temperature

0 °C

Butyllithium 1.6 M in hexane (112.5 ml, 180 mmol) and abs. ether (70 ml) was initially introduced into a 500 ml three-necked flask under an argon atmosphere and the mixture was cooled to 0° C. in an ice bath. Benzothiophene (20.1 g, 150 mmol) then dissolved in abs. ether (40 ml) and the solution added dropwise in the course of 30 minutes, while cooling with ice, and the mixture subsequently stirred in an ice bath for 2.5 h. The reaction mixture stood in a refrigerator overnight. Iodine (75.0 g) and abs. ether (50 ml) were initially introduced into a 500 ml three-necked flask under an argon atmosphere and the solution of the lithium compound was added dropwise, while cooling with ice. The mixture was warmed slowly to room temperature, hydrolysed with water and washed with sodium thiosulfate solution and the organic phase was dried over sodium sulfate. The reaction solution was then concentrated i. vac. and the residue was purified by means of flash chromatography with cyclohexane. Yield: 24.1 g (62%) semi-solid, pale brown crystals

1. temperaturewhile cooling with ice
2. customstood in a refrigerator overnight
3. temperaturewhile cooling with ice
4. washwashed with sodium thiosulfate solution
5. dry with materialthe organic phase was dried over sodium sulfate
6. concentrationThe reaction solution was then concentrated i
7. customand the residue was purified by means of flash chromatography with cyclohexane

ORD record

ord-11c7f2b59aab44ed9cdc6a92bc292763

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138187B2