Reaktionsgleichung
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C(N(C(C)C)CC)(C)C.[Br:40][C:41]1[CH:42]=[C:43]([CH:47]=[C:48]([N+:50]([O-:52])=[O:51])[CH:49]=1)[C:44](O)=[O:45]>CN(C=O)C.C(OCC)(=O)C>[Br:40][C:41]1[CH:42]=[C:43]([C:44]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:45])[CH:47]=[C:48]([N+:50]([O-:52])=[O:51])[CH:49]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
HATU (927 mg, 2.44 mmol), morpholine (0.212 mL, 2.44 mmol), and diisopropylethylamine (0.532 mL, 3.05 mmol) were added sequentially to a solution of 3-bromo-5-nitrobenzoic acid (500 mg, 2.03 mmol) in DMF (10 mL) at 0° C. The reaction mixture was stirred for 2 hours at 0° C., then the mixture was diluted with ethyl acetate (50 mL) and washed with saturated aqueous NaHCO3 (50 mL) followed by 1:1 water: brine (2×30 mL). The organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) provided (3-bromo-5-nitrophenyl)(morpholin-4-yl)methanone as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.43 (t, J=1.9 Hz, 1H), 8.28-8.12 (m, 1H), 7.89 (t, J=1.5 Hz, 1H), 3.74 (br m, 8H).
Aufarbeitung
- washwashed with saturated aqueous NaHCO3 (50 mL)
- dry with materialThe organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-64e94d6931614bcf9cb8ee22158a0fc6
- Quelldatensatz
- uspto-grants-2016_05
- Patentnummer
- US09353066B2
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