Bromochloromethane → 2-Bromo-4-methoxy-8,9-dihydro-5,7-dioxabenzocycloheptene

To a solution of 898 mg of 4-bromo-2-(2-hydroxyethyl)-6-methoxyphenol in 10 ml of DMF there was added 1 g of sodium bistrimethylsilylamide while cooling on ice, and the mixture was stirred at room temperature for 30 minutes. After adding 1 ml of bromochloromethane to the reaction mixture, it was stirred at 80° C. for 20 hours under a nitrogen atmosphere. Saturated aqueous ammonium chloride was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (420 mg) as an oil.

1. temperaturewhile cooling on ice
2. stirringwas stirred at 80° C. for 20 hours under a nitrogen atmosphere
3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
4. filtrationThe desiccating agent was filtered off
5. concentrationthe filtrate was concentrated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

ORD record

ord-b08c5e3e2d14475bbd5993c6852eadb7

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163787B2