4-Bromo-2,6-difluoroaniline → 5-Bromo-1,3-difluoro-2-nitrobenzene

Temperature

60 °C

A solution of 4-bromo-2,6-difluoroaniline (4.75 g, 22.8 mmol) in TFA (50.2 mL) and AcOH (50.2 mL) was charged with sodium perborate tetrahydrate (16.0 g, 104 mmol). The reaction was warmed to 60° C. and heated for 24 h. The reaction was quenched with water (10 mL) and extracted with EtOAc (15 mL). The organic layer was washed with brine (10 mL) and dried over anhydrous Na2SO4. The organic layer was concentrated under reduced pressure to yield a yellow solid. The material was purified by silica gel chromatography on an ISCO combi-flash Rf system using Heptane/EtOAc (100:0→90:10) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield a white solid, 2.28 g (42% yield). 1H NMR (CDCl3, 400 MHz): δ=7.31-7.35 (m, 2 H).

1. temperatureheated for 24 h
2. customThe reaction was quenched with water (10 mL)
3. extractionextracted with EtOAc (15 mL)
4. washThe organic layer was washed with brine (10 mL)
5. dry with materialdried over anhydrous Na2SO4
6. concentrationThe organic layer was concentrated under reduced pressure
7. customto yield a yellow solid
8. customThe material was purified by silica gel chromatography on an ISCO combi-flash Rf system
9. additionThe fractions containing product
10. concentrationconcentrated under reduced pressure
11. customto yield a white solid, 2.28 g (42% yield)

ORD record

ord-2af39d90a1774067a3122f196a4c40f4

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096624B2