1-Bromo-2-Chloroethane → 1-(2-Chloroethoxy)-4-iodobenzene

Temperature

100 °C

To a solution of 4-iodophenol (1.0 g) in acetonitrile (10 mL), cesium carbonate (3.0 g) and 1-bromo-2-chloroethane (0.8 g) were added and the mixture was heated to 100° C., at which it was stirred for 4 hours. Additional 1-bromo-2-chloroethane (1.0 g) was further added and stirred at 100° C. for 4 hours. The reaction mixture was cooled to room temperature and filtered to remove insoluble materials, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=11:1) to give the titled compound (0.87 g, 68%) as a yellow oil.

1. stirringstirred at 100° C. for 4 hours
2. temperatureThe reaction mixture was cooled to room temperature
3. filtrationfiltered
4. customto remove insoluble materials
5. concentrationthe filtrate was concentrated under reduced pressure
6. customThe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=11:1)

ORD record

ord-9a477358e1da400ab55e102041802214

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193176B2