Hydrochloric Acid → 2-Propoxyethyl 4-Bromobenzenesulfonate

To a solution of 2-propoxy-1-ethanol (1.5 g, 14.4 mmol) and triethylamine (2.2 g, 21.6 mmol) in dichloromethane (20 mL) at 0° C. was added 4-bromobenzenesulfonyl chloride (3.86 g, 15.1 mmol) in dichloromethane (10 mL) dropwise over 30 minutes. The reaction was then warmed to room temperature and stirred for 16 hours. The mixture was then poured into water (50 mL) and acidified with 2N aqueous hydrochloric acid (15 mL). The aqueous layer was extracted with dichloromethane and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give a crude residue. This was purified by column chromatography on silica gel (50 g), eluting with hexane:ethyl acetate (9:3), to give the title compound (2.2 g, 48%) as a colourless oil.

1. extractionThe aqueous layer was extracted with dichloromethane
2. dry with materialthe combined organic layers were dried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customto give a crude residue
6. customThis was purified by column chromatography on silica gel (50 g)
7. washeluting with hexane:ethyl acetate (9:3)

ORD-Eintrag

ord-c89d7cc853f34728b8f8c96a8a5e393d

Quelldatensatz

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06518282B1