Hydrochloric Acid → 4-Chloro-1-(1-methylethyl)-2-nitrobenzene

A solution of sodium nitrite in water (3.6 g, 52.2 mmol, 5 M, 10.4 mL) was added drop wise to a solution of 3-nitro-4-(propan-2-yl)aniline (9.4 g, 52.2 mmol) in conc. HCl (175 mL) at 0° C. and the reaction mixture was stirred at the same temperature for 1.5 h. Copper (I) chloride (8.3 g, 83.5 mmol) was then added and the solution was stirred at room temperature for 1 h and then at 80° C. for an additional hour. After cooling down the reaction mixture was extracted with DCM (3×100 mL) and the combined organic layers were dried over sodium sulfate. The crude was then purified by flash chromatography (hexane/EtOAc 95/5) to obtain the title compound as yellow oil (1.8 g, 17%).

1. stirringthe solution was stirred at room temperature for 1 h
2. waitat 80° C. for an additional hour
3. temperatureAfter cooling down the reaction mixture
4. extractionwas extracted with DCM (3×100 mL)
5. dry with materialthe combined organic layers were dried over sodium sulfate
6. customThe crude was then purified by flash chromatography (hexane/EtOAc 95/5)

ORD-Eintrag

ord-9bc867d9704d4cab86a3b57603fe5108

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09283224B2