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 fluoride (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 fluoride (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-980231efe0cb42dfb0ba3759615d54ad

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318748B2