3-Hydroxybenzaldehyde → 3-(4-Chloro-2-nitro-phenoxy)-benzaldehyde

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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]=1

Komponenten

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-ac4c381a28564f6c81080513ace2b1f2
Quelldatensatz: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08338605B2

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