5-Fluoro-2-methoxyaniline → 4-Bromo-5-fluoro-2-methoxyaniline

To a THF (20 mL) solution of 5-fluoro-2-methoxyaniline (1.76 g), a THF (30 mL) solution of pyridinium bromide perbromide (4.36 g) was added dropwise under ice-cooling, and the reaction solution was agitated for 30 minutes at room temperature. The solid which deposited from the reaction mixture was separated by filtering and the solid was washed by THF. After the obtained solid was dissolved with water and ethyl acetate, the aqueous layer was neutralized with a saturated sodium bicarbonate water, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane-ethyl acetate system), and 1.83 mg of the title compound was obtained.

1. temperaturecooling
2. customwas separated
3. filtrationby filtering
4. washthe solid was washed by THF
5. dissolutionAfter the obtained solid was dissolved with water and ethyl acetate
6. customthe organic layer was partitioned
7. washAfter the obtained organic layer was washed with a saturated saline solution, it
8. dry with materialwas dried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel chromatography (elution solvent: hexane-ethyl acetate system)

ORD record

ord-d8a3476ee8b045c8b8ecb94fd43261ad

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07880009B2