Reacción #69709

Ecuación de reacción

(2,4-bis-benzyloxy-5-bromo-phenyl)-(1,3-dihydro-isoindol-2-yl)-methanone

sodium trifluoroacetate

→

title compound

Rendimiento 29.3%

(2,4-Bis-benzyloxy-5-trifluoromethyl-phenyl)-(1,3-dihydro-isoindol-2-yl)-methanone

Rendimiento 29.3%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowere dried under vacuum (0.04 mbar) for 6 hours
2. 2
   OtroThe flask was flushed with nitrogen, DMF (5 mL)
3. 3
   workup.ADDITIONwas added
4. 4
   TemperaturaAfter cooling to r.t.
5. 5
   workup.ADDITIONthe mixture was diluted with DCM (100 mL)
6. 6
   Filtraciónfiltered through Celite
7. 7
   Lavadorinsing with DCM
8. 8
   ConcentraciónThe filtrate was concentrated to dryness
9. 9
   Otrothe residue was partially purified by flash chromatography on silica (ethyl acetate/petrol gradient, 0-20%)
10. 10
    OtroThe purest fraction was recrystallised from methanol

Procedimiento

A mixture of (2,4-bis-benzyloxy-5-bromo-phenyl)-(1,3-dihydro-isoindol-2-yl)-methanone (491 mg, 0.95 mmol), sodium trifluoroacetate (649 mg, 4.8 mmol) and copper (I) iodide (364 mg, 1.91 mmol) were dried under vacuum (0.04 mbar) for 6 hours. The flask was flushed with nitrogen, DMF (5 mL) was added and the mixture heated at 150° C. for 17 hours. After cooling to r.t., the mixture was diluted with DCM (100 mL) and filtered through Celite, rinsing with DCM. The filtrate was concentrated to dryness and the residue was partially purified by flash chromatography on silica (ethyl acetate/petrol gradient, 0-20%). The purest fraction was recrystallised from methanol to afford the title compound as a white solid (140 mg, 29%). 1H NMR (methanol-d4) 7.60 (1H, s), 7.48-7.44 (2H, m), 7.40 (2H, t), 7.37-7.21 (m, 9H), 7.17 (1H, d), 7.02 (1H, s), 5.29 (2H, s), 5.24 (2H, s), 4.88 (2H, s), 4.62 (2H, s). MS: [M+H]+ 504.

Fuente