Water → 2-Bromo-5-chloroaniline

Temperature

23 °C

A solution of 1-bromo-4-chloro-2-nitrobenzene (13.92 g, 58.87 mmol) in MeOH (300 mL) was treated with water (50 mL), ammonium chloride (22.99 g, 429.8 mmol) and iron powder (325 mesh, 16.44 g, 294.4 mmol). The suspension was stirred at 23° C. After 18 hours, the suspension was filtered through celite. The filter cake was washed with MeOH (500 mL). The combined filtrate/washings were concentrated, partitioned in EtOAc/water (500 mL/200 mL), and the organic layer was separated. The aqueous layer was extracted with EtOAc (2×200 mL). The organic layers were combined, washed with brine (200 mL), dried (MgSO4), and concentrated in vacuo affording 11.51 g of 2-bromo-5-chlorobenzenamine.

1. filtrationthe suspension was filtered through celite
2. washThe filter cake was washed with MeOH (500 mL)
3. concentrationThe combined filtrate/washings were concentrated
4. custompartitioned in EtOAc/water (500 mL/200 mL)
5. customthe organic layer was separated
6. extractionThe aqueous layer was extracted with EtOAc (2×200 mL)
7. washwashed with brine (200 mL)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in vacuo

ORD record

ord-ca515eefe6e54b38943f5da47f35843f

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07635715B2