Hydrochloric Acid → 2-Bromo-4-chloro-1-(1-methylethyl)benzene

HRID 59586

Reaktionsgleichung

[ClH:1].[Br:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[CH:10]([CH3:12])[CH3:11])N.N([O-])=O.[Na+]>O.[Cu]Cl.S(N)(=O)(=O)O>[Br:2][C:3]1[CH:4]=[C:5]([Cl:1])[CH:7]=[CH:8][C:9]=1[CH:10]([CH3:12])[CH3:11]

Komponenten

Reaktionsbedingungen

Temperatur: 5 °C

Versuchsvorschrift

Hydrochloric acid (152 g, 31% strength, 1.29 mol) was added dropwise to a suspension of 3-bromo-4-isopropylaniline (VII) (100 g, 0.43 mol) and water (150 g) at room temperature. The suspension was subsequently cooled to 5° C. and a solution of sodium nitrite (32.7 g, 0.46 mol) in water (140 g) was added dropwise over a period of 2 hours. After stirring for another 1 hour, amidosulphuric acid (2.5 g, 0.026 mol) was added. Copper(I) chloride (10.8 g, 0.11 mol), hydrochloric acid (202 g, 31%, 1.72 mol) and water (75 g) were placed in a second flask and the diazonium salt generated previously was added dropwise over a period of 30 minutes. After stirring for another 1.5 hours, the mixture was extracted with dichloromethane (250 g), the phases were separated and dichloromethane was distilled off under reduced pressure. The crude product obtained was purified by distillation. 2-Bromo-4-chloro-1-isopropylbenzene (62.6 g, 94.8 GC-% by area. 59% of theory) was obtained as a colourless oil.

Aufarbeitung

stirringAfter stirring for another 1.5 hours
extractionthe mixture was extracted with dichloromethane (250 g)
customthe phases were separated
distillationdichloromethane was distilled off under reduced pressure
customThe crude product obtained
distillationwas purified by distillation

Quellen und Nachweise

ORD-Eintrag: ord-75e5646be5c9480fba177cf39bd72a36
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09440908B2

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