Hydrochloric Acid → 4-Bromo-2-cyclobutoxyphenol

To 7.26 g (25.3 mmol) of 4-bromo-2-cyclobutoxy-1-methoxymethoxybenzene obtained in Reference Example 5-(c) was added 30 ml of 1,4-dioxane solution containing 4N hydrogen chloride, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, 100 ml of water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=9:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 3.07 g of the title compound as a pale yellowish oil. (Yield: 50%)

1. additionwas added to the reaction mixture
2. extractionthe mixture was extracted with diethyl ether
3. customThe organic layer after separation
4. washwas washed with a saturated aqueous solution of sodium chloride
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. additionthe fractions containing the desired compound
8. concentrationwere concentrated under reduced pressure

ORD record

ord-546deae8ba784ff8b210f77c2e169cf2

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450319B2