({3-Bromo-5-cyano-2-[(trifluoroacetyl)amino]phenyl}methyl)(triphenyl)phosphonium bromide → HCID 58138925, compound

Temperature

130 °C

({3-bromo-5-cyano-2-[(trifluoroacetyl)amino]phenyl}methyl)(triphenyl)phosphonium bromide (Intermediate 3, 37.2 g) was dissolved in DMF (150 mL) and the reaction mixture was heated to 130° C. stirring for 3 h. The reaction mixture was allowed to cool to room temperature then quenched with water (400 mL). The reaction mixture was then extracted with ethyl acetate (3×300 mL). The organic extract was washed with a 1:1 mixture of water:brine (2×600 mL), dried (MgSO4), filtered and the solvent was removed. The resulting residues were then purified by filtration through a pad of silica gel eluting with 2-10% EtOAc:isoHexane. Fractions 1 to 4 were combined and the solvent was removed to give the title compound as an off-white solid (6 g);

1. temperatureto cool to room temperature
2. customthen quenched with water (400 mL)
3. extractionThe reaction mixture was then extracted with ethyl acetate (3×300 mL)
4. extractionThe organic extract
5. washwas washed with a 1:1 mixture of water
6. dry with materialbrine (2×600 mL), dried (MgSO4)
7. filtrationfiltered
8. customthe solvent was removed
9. filtrationThe resulting residues were then purified by filtration through a pad of silica gel eluting with 2-10% EtOAc
10. customthe solvent was removed

ORD record

ord-f417920bd68343158e03e9e1c27290be

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829031B2