Hydrochloric Acid → 2-{4-[(Trifluoromethyl)sulfanyl]phenyl}ethan-1-amine

4-(Trifluoromethylthio)phenylacetonitrile (183.4 mg, 0.844 mmol), 0.3 molar in THF, was heated to reflux and then treated with Borane-methyl sulfide complex (88.09 μL, 0.929 mmol). After 1 hour of refluxing, the reaction mixture was cooled to ambient temperature and then treated dropwise with 5.0 molar hydrochloric acid (607.9 μL, 3.040 mmol). The reaction mixture was then heated to reflux for an additional 30 minutes. After 30 minutes the reaction mixture was cooled to 0° C. and then treated with 1.0 molar sodium hydroxide (4644 μL, 4.644 mmol). The reaction mixture was diluted with diethyl ether and partitioned with deionized water. The organic layer was dried with potassium carbonate 98% powder, filtered, concentrated, and dried for one minute under high vacuum to provide the title compound (170.7 mg, 0.772 mmol, 91.2% yield) as a light yellow oil.

1. temperatureto reflux
2. additiontreated with Borane-methyl sulfide complex (88.09 μL, 0.929 mmol)
3. temperatureAfter 1 hour of refluxing
4. temperatureThe reaction mixture was then heated
5. temperatureto reflux for an additional 30 minutes
6. temperatureAfter 30 minutes the reaction mixture was cooled to 0° C.
7. custompartitioned with deionized water
8. dry with materialThe organic layer was dried with potassium carbonate 98% powder
9. filtrationfiltered
10. concentrationconcentrated
11. customdried for one minute under high vacuum

ORD record

ord-c6783d31cb8545de8869b892c4c675fa

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096567B2