Hydrochloric Acid → 2-bromo-N1,N1-dihexylbenzene-1,4-diamine

Temperature

65 °C

A mixture of concentrated hydrochloric acid (4.0 mL), water (100 mL) and iron powder (13.44 g, 241 mmol) was stirred at 65° C. for 15 min. The aqueous layer of the mixture was poured out, and a solution of 2-bromo-N,N-dihexyl-4-nitroaniline (9.28 g, 24.1 mmol) in MeOH (150 mL) was added to the above processed iron powder. The mixture was acidified to pH 3 with hydrochloric acid and stirred at 65° C. for 30 min. The mixture was then cooled to rt, adjusted to pH 10 with Et3N and filtered and the filtrate was concentrated. The residue was dissolved in 150 mL of DCM and the solution was washed with water (100 mL×3) and brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=20:1) to give the title compound as colorless oil (4.40 g, 51%).

1. additionThe aqueous layer of the mixture was poured out
2. stirringstirred at 65° C. for 30 min
3. temperatureThe mixture was then cooled to rt
4. filtrationfiltered
5. concentrationthe filtrate was concentrated
6. dissolutionThe residue was dissolved in 150 mL of DCM
7. washthe solution was washed with water (100 mL×3) and brine (100 mL)
8. dry with materialdried over anhydrous Na2SO4
9. concentrationconcentrated in vacuo
10. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=20:1)

ORD record

ord-850cf7dfc333437e866dd74c83c17dad

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434695B2