Ethylene Oxide → N-[2-[2-Bromo-1-(3-methoxyphenyl)ethoxy]ethyl]-4-nitro-benzenesulfonamide

참여 물질

반응 조건

반응 단계

Add ethylene oxide (11 mL, 220 mmol) all at once to DCM cooled to 0° C.; then add 1-methoxy-3-vinylbenzene (7.09 g, 52.82 mmol) via a syringe. Stir the mixture while maintaining it 0° C. Add N-bromosuccinimide (9.4 g, 52.82 mmol) and 4-nitrobenzenesulfonamide (8.9 g, 44.02 mmol). Wrap flask in foil and stir the reaction mixture for 20 h while maintaining it at ambient temperature. Concentrate under reduced pressure; filter; and concentrate the filtrate under reduced pressure to provide a residue. Purify the residue via flash column chromatography eluting with a 5-40% gradient of EtOAc in hexanes. Combine the product fractions, and remove the solvents under reduced pressure to provide the title compound as a dark yellow oil (14.22 g, 70.3%). MS (m/z): 459 (M+1).

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