p-Bromobenzenesulfonyl chloride → 2-Cyclohexyloxyethyl 4-bromobenzenesulfonate

A solution of 2-cyclohexyloxyethanol (4.56 g, 32 mmol) and triethylamine (22 mL, 160 mmol) in dichloromethane (225 mL) was stirred under nitrogen. A saturated solution of 4-bromobenzenesulfonyl chloride (9.0 g, 35 mmol) in dichloromethane was added dropwise at 0° C., and the reaction mixture was stirred overnight under nitrogen. The reaction mixture was then washed with 1N aqueous hydrochloric acid (2×200 mL) and the organic layer separated. The organic layer was washed sequentially with water (200 mL) and brine (200 mL), dried (MgSO4) and then concentrated in vacuo to give a white solid. The crude solid was dissolved in the minimum amount of dichloromethane and purified by passing through a plug of silica, which was eluted with ethyl acetate:hexane (50:50), ethyl acetate (100%) and finally methanol:ethyl acetate (10:90). The title compound was obtained as a yellow oil (4.3 g, 41%).

1. washThe reaction mixture was then washed with 1N aqueous hydrochloric acid (2×200 mL)
2. customthe organic layer separated
3. washThe organic layer was washed sequentially with water (200 mL) and brine (200 mL)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated in vacuo
6. customto give a white solid
7. custompurified
8. washwas eluted with ethyl acetate:hexane (50:50), ethyl acetate (100%) and finally methanol:ethyl acetate (10:90)

ORD record

ord-0162e08057fe4f97a4e2bff84756020c

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07012083B2