Hydrochloric Acid → HCID 90410767, compound

Temperature

-40 °C

In a nitrogen atmosphere, 10.00 g of 3,5-difluoro-1-(4-propylphenyl)benzene was dissolved in 50 mL of THF, and the resultant solution was cooled to −40° C. Then, 30 mL of butyl lithium (1.6 mol/L, hexane solution) was added at such a rate that the inside temperature did not exceed −35° C. After stirring at −40° C. for 1 hour, 5.37 g of trimethoxyborane was added at such a rate that the inside temperature did not exceed −35° C. After stirring at −40° C. for 1 hour, the inside temperature was increased to room temperature, and 10% hydrochloric acid was added until the reaction system became acidic. Then, an organic layer was separated from the mixture, and an aqueous layer was subjected to extraction with toluene. The toluene extract was combined with the organic layer and cooled with ice, and 11.71 g of a 15% aqueous hydrogen peroxide solution was added to the mixture, followed by stirring at room temperature for 15 hours. Further, an organic layer was separated from the mixture, and an aqueous layer was subjected to extraction with toluene. The toluene extract was combined with the organic layer and washed with a 10% aqueous sodium sulfite solution and saturated brine. The resultant mixture was dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to yield 10.24 g of 2,6-difluoro-4-(4-propylphenyl)phenol.

1. customdid not exceed −35° C
2. customdid not exceed −35° C
3. stirringAfter stirring at −40° C. for 1 hour
4. temperaturethe inside temperature was increased to room temperature
5. customThen, an organic layer was separated from the mixture
6. extractionan aqueous layer was subjected to extraction with toluene
7. extractionThe toluene extract
8. temperaturecooled with ice, and 11.71 g of a 15% aqueous hydrogen peroxide solution
9. additionwas added to the mixture
10. stirringby stirring at room temperature for 15 hours
11. customFurther, an organic layer was separated from the mixture
12. extractionan aqueous layer was subjected to extraction with toluene
13. extractionThe toluene extract
14. washwashed with a 10% aqueous sodium sulfite solution and saturated brine
15. dry with materialThe resultant mixture was dried
16. additionby adding sodium sulfate
17. distillationthe solvent was distilled off under reduced pressure
18. customThe residue was recrystallized from ethanol

ORD record

ord-22ca1f0cb0ce44ddbe3848c61f3231a2

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916718B2