2-Bromo-4-nitro-1-(propan-2-yl)benzene → 3-Bromo-4-isopropylaniline

2-Bromo-1-isopropyl-4-nitrobenzene (XI) (20 g, 78.1 mmol, 95.8 GC % by area), methanol (400 ml), platinum on carbon (5% of platinum, poisoned with sulphur, moist with water) (1.0 g, 0.090 mmol) and zinc dibromide (265 mg, 1.18 mmol) were placed in a 600 ml autoclave. The autoclave was subsequently flushed with nitrogen and pressurized to 5 bar with hydrogen at room temperature. The contents of the autoclave were filtered through Celite, washed with methanol and the solvent was distilled off under reduced pressure. 3-Bromo-4-isopropylaniline (17.4 g, 94.5 LC-% by area, 97.7 GC-% by area, >99% of theory) was obtained as a brown oil.

1. customThe autoclave was subsequently flushed with nitrogen
2. custompressurized to 5 bar with hydrogen at room temperature
3. filtrationThe contents of the autoclave were filtered through Celite
4. washwashed with methanol
5. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-532af21f19f842208c8ea50eafe144de

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09440908B2