Hydrogen Peroxide → HCID 67059678, compound

Temperature

-50 °C

225 mL of 2.67 M butyllithium hexane solution was added dropwise to THF (500 mL) solution containing 96.0 g of 1-(2-butenoxy)-2,3-difluorobenzene under vigorous stirring at −50° C. or lower, while keeping the internal temperature, and then the stirring was continued for 1 hour at −50° C. While keeping the internal temperature, THF (60 mL) solution containing 63.3 g of trimethyl borate was added dropwise. The stirring was continued for 30 minutes while keeping the temperature, and then the temperature was increased to 0° C. While keeping the internal temperature, 120 mL of water was added dropwise, and then 160 mL of 15% hydrogen peroxide solution was further added dropwise. The stirring was continued for 1 hour at 0° C. The solution was heated to room temperature, and the stirring was further continued for 2 hours. Then, saturated saline was added to separate the organic phase, and extraction was performed from the water phase with toluene (twice). The organic phase was collected, then washed with 10% sodium thiosulfate aqueous solution, 3M hydrochloric acid, water, saturated aqueous solution of sodium hydrogencarbonate, and saturated saline in this order, and dried over anhydrous magnesium sulfate. The solvent was evaporated. The obtained residue was purified by column chromatography, and was subjected to recrystallization, to thereby obtain 42.7 g of 4-(2-butenoxy)-2,3-difluorophenol in the form of pale yellow needle-like crystals (E/Z ratio=99/1, according to 1H-NMR analysis).

1. additionwas added dropwise
2. waitThe stirring was continued for 30 minutes
3. temperaturethe temperature was increased to 0° C
4. additionwas added dropwise
5. waitThe stirring was continued for 1 hour at 0° C
6. temperatureThe solution was heated to room temperature
7. waitthe stirring was further continued for 2 hours
8. additionThen, saturated saline was added
9. customto separate
10. extractionthe organic phase, and extraction
11. customThe organic phase was collected
12. washwashed with 10% sodium thiosulfate aqueous solution, 3M hydrochloric acid, water, saturated aqueous solution of sodium hydrogencarbonate, and saturated saline in this order
13. dry with materialdried over anhydrous magnesium sulfate
14. customThe solvent was evaporated
15. customThe obtained residue was purified by column chromatography
16. customwas subjected to recrystallization

ORD record

ord-cc9f24d5730c492ebbda9bdac3281178

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07651630B2