Hydrochloric Acid → HCID 66603169, compound

Temperature

80 °C

To 21.9 g (94.9 mmol) of 4-bromo-2-isopropoxyphenol obtained in Reference Example 6-(a) were added 2.01 g (9.56 mmol) of tetraethylammonium bromide, 150 ml of 1,4-dioxane, 11.2 g (275 mmol) of sodium hydroxide and 10 ml of water, and the mixture was stirred at 80° C. Then, the mixture was stirred at the same temperature for 1 hour while blowing 40.4 g of chlorodifluoromethane therein. After completion of the reaction, water was added to the reaction mixture, a pH of the mixture was adjusted to 7 with conc. hydrochloric acid, and extracted with ethyl acetate. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=100:1→25:1 (V/V)), and the obtained crude oil containing the desired compound was applied to distillation under reduced pressure (105 to 110° C./7 Pa) to obtain 8.27 g of the title compound as a colorless oil. (Yield: 31%)

1. stirringThen, the mixture was stirred at the same temperature for 1 hour
2. additionwas added to the reaction mixture
3. extractionextracted with ethyl acetate
4. customThe organic layer after separation
5. washwas washed with a saturated aqueous solution of sodium chloride
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customthe obtained crude oil

ORD record

ord-621cd8eafd514cf9b144efe0400fa584

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450319B2