Реакция #69709

Уравнение реакции

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

sodium trifluoroacetate

→

title compound

Выход 29.3%

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

Выход 29.3%

Условия реакции

Обработка

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

Методика

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.

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