2-Bromo-4-nitro-1-[(propan-2-yl)oxy]benzene → 3-Bromo-4-(1-methylethoxy)benzenamine

Platinum oxide (50 mg) was added to a solution of 2-isopropoxy-5-nitrobromobenzene (1.7 g, 6.5 mmol) in ethyl acetate (50 ml) and the mixture was stirred under hydrogen (50 psi) for 1 hour. The mixture was filtered, further platinum oxide (50 mg) was added and the mixture was stirred under hydrogen (50 psi) for 1 hour. The mixture was filtered and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography, eluting with hexane/EtOAc (80:20), to give the title compound (0.92 g, 62%); δH (360MHz, CDCl3) 1.32 (3H, d, J 5.6Hz, OCH(CH3)2), 4.33 (1H, m, OCH(CH3)2), 6.57 (1H, dd, J 8.7, 2.8Hz, 6-H), 6.78 (1H, d, J 8.7Hz, 5-H), 6.91 (1H, d, J 2.8 Hz, 2-H).

1. filtrationThe mixture was filtered
2. additionfurther platinum oxide (50 mg) was added
3. stirringthe mixture was stirred under hydrogen (50 psi) for 1 hour
4. filtrationThe mixture was filtered
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by flash chromatography
7. washeluting with hexane/EtOAc (80:20)

ORD record

ord-8f17b1cf9eb04de6ba5a39a6d9eeed6f

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06071928