1,4-Dibromobenzene → HCID 86590558, compound

Temperature

-78 °C

To a −78° C. solution of 1,4-dibromobenzene (330 mg) in THF (5.2 mL) was added 2.5M n-BuLi in hexanes (0.52 mL) and the solution was aged for 30 minutes. Then, a solution of (2S)-1-((tert-butyl(dimethyl)silyl)oxy)-4,4-difluoro-N-((1E)-2,2,2-trifluoroethylidene)pentan-2-amine (333 mg) in THF (5.2 mL) was added. The mixture was stirred at −78° C. for 45 minutes, then poured over cold saturated ammonium chloride, extracted with ethyl acetate (2×), washed with brine, dried over magnesium sulfate, filtered and the solvent evaporated under vacuum. The residue was dissolved in THF (10 mL) cooled in an ice/water bath and n-tetrabutylammonium fluororide (1M in THF, 1.5 mL) was added. The mixture was stirred at 0° C. for 1 h, poured over cold water, extracted with ethyl acetate (2×), washed with brine, dried over magnesium sulfate, filtered and the solvent evaporated under vacuum to afford (2S)-2-(((1S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl)amino)-4,4-difluoropentan-1-ol.

1. extractionextracted with ethyl acetate (2×)
2. washwashed with brine
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. customthe solvent evaporated under vacuum
6. dissolutionThe residue was dissolved in THF (10 mL)
7. temperaturecooled in an ice/water bath
8. additionn-tetrabutylammonium fluororide (1M in THF, 1.5 mL) was added
9. stirringThe mixture was stirred at 0° C. for 1 h
10. additionpoured over cold water
11. extractionextracted with ethyl acetate (2×)
12. washwashed with brine
13. dry with materialdried over magnesium sulfate
14. filtrationfiltered
15. customthe solvent evaporated under vacuum

ORD record

ord-95ee7908e2e6485da11c227989058d00

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772336B2