Thionyl Chloride → 2-(4-Iodophenyl)ethylchloride

To a 500 mL round-bottomed flask equipped with dropping funnel, condenser and N2 inlet were added 307 g (124 mmol) 2-(4-iodophenyl)ethanol, 200 mL chloroform, and 10.0 mL (124 mmol) pyrdine. A solution of 13.5 mL (186 mmol) thionyl chloride in 50 mL chloroform was added dropwise over 15 min, and the reaction then heated at reflux for 2 hr. The reaction was cooled, the solvent evaporated, and the residue taken up in ethyl acetate, washed with 1 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and brine, dried, and evaporated. The resulting oil was chromatographed on silica gel using 20% ethyl acetate in hexane as eluant to afford 32.6 g (99%) of the product as an oil.

1. customTo a 500 mL round-bottomed flask equipped
2. customthe reaction
3. temperaturethen heated
4. temperatureat reflux for 2 hr
5. temperatureThe reaction was cooled
6. customthe solvent evaporated
7. washwashed with 1 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and brine
8. customdried
9. customevaporated
10. customThe resulting oil was chromatographed on silica gel using 20% ethyl acetate in hexane as eluant

ORD record

ord-bc4b65c8bd1c440e81b832cfad53917d

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06465491B2