3-Hydroxybenzaldehyde → 3-(4-Chloro-2-nitro-phenoxy)-benzaldehyde
Reaktionsgleichung
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[CH:16]=[O:17])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 85 °C
Versuchsvorschrift
To a solution of DMF (50 mL) was added 1-bromo-2-nitro-4-chloro-benzene (10.0 g, 42.2 mmol), 3-hydroxybenzaldehyde (5.2 g, 42.2 mmol), and K2CO3 (11.5 g, 84.6 mmol). The solution was heated to 85° C. and stirred overnight. The reaction was poured into distill water and extracted with ethyl acetate. The combined organic layers were washed with distilled water, brine, and dried over Na2SO4, filtered and concentrated under vacuum giving the crude title compound. This solid was purified by silica gel column chromatography eluting with hexanes/ethyl acetate (4:1) to give the title compound (4.4 gm, 41%).
Aufarbeitung
- additionThe reaction was poured
- distillationinto distill water
- extractionextracted with ethyl acetate
- washThe combined organic layers were washed with distilled water, brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
- customgiving the crude title compound
- customThis solid was purified by silica gel column chromatography
- washeluting with hexanes/ethyl acetate (4:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-945b1e6ae39a4faea15462eb64128afc
- Quelldatensatz
- uspto-grants-2010_07
- Patentnummer
- US07763731B2
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