Hydrogen Bromide → 4-Bromo-3-fluoro-2-methoxyaniline

To a solution of 2-methoxy-3-fluoroaniline (2.18 g, 15.46 mmol) in AcOH (10 mL) was added a solution of bromine (1.98 g, 12.37 mmol) in AcOH (2 mL) dropwise. The reaction mixture was stirred at room temperature for 30 minutes. The resulting solid was filtered and washed with acetic acid to give the title and a di-bromo-compound as the HBr salt. The solid (2.53 g) was dissolved in water, basified by addition of KOH, and extracted with EtOAc. The organic layer was dried with Na2SO4 and concentrated in vacuo. The residue was purified by Biotage silica gel column chromatography eluting with 15% EtOAc in cyclohexanes to give the title compound as white solid (1.24 g, 36%).

1. filtrationThe resulting solid was filtered
2. washwashed with acetic acid
3. customto give the title
4. extractionextracted with EtOAc
5. dry with materialThe organic layer was dried with Na2SO4
6. concentrationconcentrated in vacuo
7. customThe residue was purified by Biotage silica gel column chromatography
8. washeluting with 15% EtOAc in cyclohexanes

ORD record

ord-e0138f9c7a574c72a15a600bb67d7e69

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09334286B2