Trifluoroacetic acid → 2-(Benzyloxy)-5-nitroaniline
Reaktionsgleichung
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[NH:18]C(=O)OC(C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.CCCCCC.C(OCC)(=O)C>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[NH2:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of tert-butyl (2-(benzyloxy)-5-nitrophenyl)carbamate (1.0 g) in DCM (10 mL), cooled to 0° C., was added trifluoroacetic acid (5.0 mL). The reaction mixture was stirred at 0° C. for 15 minutes and then at room temperature for 30 minutes. The reaction was monitored by TLC using hexane:ethyl acetate (3:7) as mobile phase. After completion, the reaction mixture was quenched in water and neutralized with sodium bicarbonate. Product was extracted into DCM. The organic layer was washed with brine, dried over sodium sulfate and concentrated completely under reduce pressure at 40° C. Crude material was purified by trituration with diethyl ether to give 0.7 g of 2-(benzyloxy)-5-nitroaniline. 1H NMR: DMSO-d6 (400 MHz): 5.26 (s, 2H), 5.44 (s, 2H), 7.04 (d, 1H, J=8.8), 7.34 (m, 1H), 7.45 (m, 3H), 7.50 (s, 1H), 7.520 (d, 2H, J=2.8).
Aufarbeitung
- waitat room temperature for 30 minutes
- customAfter completion, the reaction mixture was quenched in water and neutralized with sodium bicarbonate
- extractionProduct was extracted into DCM
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated completely
- customat 40° C
- customCrude material was purified by trituration with diethyl ether
Quellen und Nachweise
- ORD-Eintrag
- ord-62b74d0e0b8641c084ce22d28188c036
- Quelldatensatz
- uspto-grants-2015_09
- Patentnummer
- US09126950B2
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