반응 #69709

반응 방정식

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

sodium trifluoroacetate

→

title compound

수율 29.3%

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

수율 29.3%

반응 조건

후처리

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

실험 절차

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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