Borane → HCID 66970376, compound

To the solid 2-methyl-2-(2-nitro-4-trifluoromethyl-phenyl)-propionitrile (1.0 g, 3.9 mmol) in a 250 mL round-bottom flask at 0 degrees C. was added a solution of borane in THF (47 mL of a 1 M solution in THF, 47 mmol). The orange-yellow solution was allowed to warm to room temperature and stir for 6 h. The solution was then cooled to 0 degrees C., and was quenched by the careful dropwise addition of 6 N HCl. After gas evolution ceased, a total of 47 mL 6N HCl was added, resulting in a white precipitate. The mixture was concentrated in vacuo to ½ the original volume, and was basified at 0 degrees C. with 6N NaOH. The mixture was extracted with a 100 mL portion of ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give a yellow oil. Purification by flash chromatography provided the desired product which contained minor impurities by NMR. MS m/z 263=[M+H]+. Calc'd for C11H13F3N2O2: 262.23.

1. customat 0 degrees C
2. temperatureThe solution was then cooled to 0 degrees C
3. custom, and was quenched by the careful dropwise addition of 6 N HCl
4. additiona total of 47 mL 6N HCl was added
5. customresulting in a white precipitate
6. concentrationThe mixture was concentrated in vacuo
7. customwas basified at 0 degrees C
8. extractionThe mixture was extracted with a 100 mL portion of ethyl acetate
9. dry with materialThe organic layer was dried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customto give a yellow oil
13. customPurification by flash chromatography

ORD record

ord-15caaf68269f4f9bb91032175d7cd693

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07880000B2