反応 #69709

反応方程式

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

sodium trifluoroacetate

→

title compound

収率 29.3%

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

収率 29.3%

反応条件

後処理

1. 1
   その他were dried under vacuum (0.04 mbar) for 6 hours
2. 2
   その他The flask was flushed with nitrogen, DMF (5 mL)
3. 3
   workup.ADDITIONwas added
4. 4
   温度After cooling to r.t.
5. 5
   workup.ADDITIONthe mixture was diluted with DCM (100 mL)
6. 6
   ろ過filtered through Celite
7. 7
   洗浄rinsing with DCM
8. 8
   濃縮The filtrate was concentrated to dryness
9. 9
   その他the residue was partially purified by flash chromatography on silica (ethyl acetate/petrol gradient, 0-20%)
10. 10
    その他The purest fraction was recrystallised from methanol

実験手順

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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