Iodine → HCID 57571706, compound

Temperature

-30 °C

To 76 ml of diethyl ether solution containing 24.1 g (84 mmol) of 1-bromo-2-cyclopropylmethoxy-3-methoxymethoxybenzene obtained in Reference example 12-(a) was added dropwise 53.4 ml (84 mmol) of 1.58M n-butyl lithium hexane solution at −60° C. or lower under argon atmosphere. The mixture was stirred at the same temperature for further 30 minutes, raised to −30° C., and then, 50 ml of diethyl ether solution containing 21.3 g (84 mmol) of iodine was added dropwise to the mixture. After completion of the dropwise addition, the mixture was stirred at the same temperature for 30 minutes, and then, gradually raised to room temperature. After completion of the reaction, to the reaction mixture was added 95 ml of 2% aqueous sodium thiosulfate solution, and the mixture was stirred for 1 hour. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 29.8 g of the title compound as a reddish oil substantially quantitatively.

1. customobtained in Reference example 12-(a)
2. additionwas added dropwise to the mixture
3. additionAfter completion of the dropwise addition
4. stirringthe mixture was stirred at the same temperature for 30 minutes
5. temperaturegradually raised to room temperature
6. customAfter completion of the reaction
7. stirringthe mixture was stirred for 1 hour
8. customThe organic layer after separation
9. washwas washed with a saturated aqueous solution of sodium chloride
10. customdried
11. dry with materialover dried over anhydrous sodium sulfate
12. concentrationconcentrated under reduced pressure

ORD record

ord-d066b67e4fb841d783ff7518dd688aa5

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450319B2