Formamidine acetate → 5-Bromo-2-chloro-4-methylaniline

Temperatur

80 °C

In an autoclave, a mixture of 253 mmol of 1-bromo-4-chloro-2-methyl-5-nitro-benzene [10289-13-1], 2 g of Raney nickel (60% aqueous) and 1.5 g of formamidine acetate in 102 ml of methanol is stirred under an atmosphere of hydrogen (pressure 12 bars) at 80° C. for 1 hour. The mixture is cooled to room temperature, filtered and evaporated. The residue is partitioned between aqueous saturated sodium bicarbonate-solution and tert-butyl-methyl ether. The aqueous phase is extracted with tert-butyl-methyl ether. The combined organic phases are dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (SiO2 60 F) to afford the title compound which is identified based on the Rf value.

1. temperatureThe mixture is cooled to room temperature
2. filtrationfiltered
3. customevaporated
4. customThe residue is partitioned between aqueous saturated sodium bicarbonate-solution and tert-butyl-methyl ether
5. extractionThe aqueous phase is extracted with tert-butyl-methyl ether
6. dry with materialThe combined organic phases are dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe resulting residue is purified by flash chromatography (SiO2 60 F)

ORD-Eintrag

ord-69868a80d91e4c45b105acffa6c78cd7

Quelldatensatz

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08324235B2