Hydrochloric Acid → 4-(Trifluoromethyl)phenylboronic acid

33 g (0.15 mol) of 4-bromotrifluoromethylbenzen was put into a 500-mL three-neck flask, and nitrogen substitution in the system was carried out. Then, 200 mL of tetrahydrofuran (THF) was added thereto, and the mixture was stirred. This mixture solution was stirred at −78° C., and 100 mL (0.16 mol) of n-butyllithium (1.6 mol/L) was dropped into the solution through a dropping funnel. After that, the obtained solution was stirred at the same temperature for 1 hour, and 22.3 mL (0.20 mol) of trimethyl borate was added to be stirred for about 12 hours while the reaction temperature was allowed to gradually increase to the room temperature. Then, 100 mL of dilute hydrochloric acid (1 mol/L) was added to the reaction solution, and the solution was stirred for 1 hour. A water layer of the mixture was extracted using ethyl acetate three times, the extracted solution and an organic layer were washed together one time using saturated saline, and the organic layer was dried with magnesium sulfate. The mixture was filtrated naturally to remove magnesium sulfate, and the filtrate was condensed to obtain a solid. The solid was washed with chloroform, whereby 15 g of a white solid, which was a target matter, was obtained with the yield of 54%.

1. stirringThis mixture solution was stirred at −78° C.
2. stirringAfter that, the obtained solution was stirred at the same temperature for 1 hour
3. stirringto be stirred for about 12 hours while the reaction temperature
4. stirringthe solution was stirred for 1 hour
5. extractionA water layer of the mixture was extracted
6. washthe extracted solution and an organic layer were washed together one time
7. dry with materialthe organic layer was dried with magnesium sulfate
8. filtrationThe mixture was filtrated naturally
9. customto remove magnesium sulfate
10. customcondensed
11. customto obtain a solid
12. washThe solid was washed with chloroform, whereby 15 g of a white solid, which
13. customwas obtained with the yield of 54%

ORD record

ord-38c2cb59913c49d8ad89261bbe6e5e7c

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08183793B2