Stannous Chloride → 4-Bromo-2-ethoxyaniline

Temperature

70 °C

To a solution of 4-bromo-2-ethoxy-1-nitrobenzene (Preparation 100, 250 mg, 1.016 mmol) in EtOH (15 mL) was added tin (II) chloride (963 mg, 5.08 mmol). The reaction mixture was heated to 70° C. for 2 hours. The reaction mixture was diluted with ice-water (10 mL) and concentrated in vacuo. Aqueous Na2CO3 (2M, 20 mL) was added and the reaction mixture was extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine (30 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by passage through a SCX-2 cartridge eluting with 100% MeOH—1M NH3 in MeOH to give the title compound (179 mg, 82%).

1. concentrationconcentrated in vacuo
2. additionAqueous Na2CO3 (2M, 20 mL) was added
3. extractionthe reaction mixture was extracted with EtOAc (3×20 mL)
4. washThe combined organic layers were washed with brine (30 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo
7. customThe residue was purified by passage through a SCX-2 cartridge
8. washeluting with 100% MeOH—1M NH3 in MeOH

ORD record

ord-747baf79925042a3bc13a5cdebccc696

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409907B2