Reaktionsgleichung
[C:1]([C:3]1[C:4]([Cl:12])=[C:5]([CH:7]=[C:8]([F:11])[C:9]=1[Cl:10])N)#[N:2].Cl.O.N([O-])=O.[Na+].O.[BrH:20]>>[C:1]([C:3]1[C:4]([Cl:12])=[C:5]([Br:20])[CH:7]=[C:8]([F:11])[C:9]=1[Cl:10])#[N:2]Komponenten
Reaktionsbedingungen
- Temperatur
- 2.5 °C
Versuchsvorschrift
47.2 g of 3-cyano-2,4-dichloro-5-fluoroaniline (0.23 mol) were added to a solution of 150 ml of hydrochloric acid-water (1:1). The resulting mixture was stirred to be a slurry and then cooled to 0-5° C. A solution of sodium nitrite (16.7 g, 0.242 mol) and water (46 ml) was added thereto over 30 minutes. The resulting solution was added to a solution of cuprous bromide (0.275 mol) in 147 ml of hydrobromic acid. The reaction mixture was stirred for 2 hours and allowed overnight. The resulting mixture was wet-distilled. The distilled fraction was extracted with toluence. The oil layer was washed successively with 10% aqueous solution of NaOH, concentrated sulfuric acid and water, and dried over anhydrous sodium sulfate. After removing the solvent, the residue was crystallized from toluene to give 53.3 g of 3-cyano-2,4-dichloro-5-fluorobromobenzene (0.198 mol) in 86.2% yield.
Aufarbeitung
- stirringThe reaction mixture was stirred for 2 hours
- waitallowed overnight
- distillationThe resulting mixture was wet-distilled
- extractionThe distilled fraction was extracted with toluence
- washThe oil layer was washed successively with 10% aqueous solution of NaOH, concentrated sulfuric acid and water
- dry with materialdried over anhydrous sodium sulfate
- customAfter removing the solvent
- customthe residue was crystallized from toluene
Quellen und Nachweise
- ORD-Eintrag
- ord-f6ad75e6f33a41e3a3fc7e6b19cfe702
- Quelldatensatz
- uspto-grants-2004_03
- Patentnummer
- US06699992B2
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