Ammonium Chloride → 5-Bromo-2-chlorobenzaldehyde
Reaktionsgleichung
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:9]=[CH:10][C:11]([Cl:20])=[C:12]([CH:19]=1)[C:13](N(OC)C)=[O:14].[Cl-].[NH4+]>O1CCCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([Cl:20])=[C:12]([CH:19]=1)[CH:13]=[O:14]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -15 °C
Versuchsvorschrift
LiAlH4 (1.47 g, 0.0388 mol) was added little by little to a tetrahydrofuran (108 mL) solution of 5-bromo-2-chloro-N-methoxy-N-methylbenzamide (10.8 g, 0.0388 mol) so that the internal temperature did not exceed −10° C. The reaction mixture was stirred at −15° C. for one hour and carefully added with a saturated ammonium chloride aqueous solution and deposited insolubles were filtered off with celite. After the filtrate was extracted with ethyl acetate, the organic layer was washed with 1M hydrochloric acid, a saturated sodium bicarbonate aqueous solution, brine, and then dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the solvent was evaporated under reduced pressure to obtain 5-bromo-2-chlorobenzaldehyde (8.1 g, 95%) as a pale yellow crystal. This was used in the next reaction without purification.
Aufarbeitung
- customdid not exceed −10° C
- filtrationwere filtered off with celite
- extractionAfter the filtrate was extracted with ethyl acetate
- washthe organic layer was washed with 1M hydrochloric acid
- dry with materiala saturated sodium bicarbonate aqueous solution, brine, and then dried with anhydrous magnesium sulfate
- filtrationAfter the desiccant was filtered off
- customthe solvent was evaporated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-c4be4ed25582465ea3f97b76710a0f2c
- Quelldatensatz
- uspto-grants-2011_03
- Patentnummer
- US07910619B2
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