Methanol → 5-Bromo-3-fluoro-2-nitroanisole

Temperature

90 °C

A solution of 5-bromo-1,3-difluoro-2-nitrobenzene (Compound 146H, 2.00 g, 8.40 mmol) in MeOH (15.0 mL) was added potassium hydroxide (504 mg, 8.98 mmol). The reaction was stirred at 90° C. for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was diluted with EtOAc (15 mL), washed with water (10 mL), washed with brine (10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield a yellow solid. The crude material was purified by silica gel chromatography on an ISCO combi-flash Rf system using Heptane/EtOAc (100:0→70:30) as eluent to yield the desired product as a light yellow solid 1.75 g (83% yield). 1H NMR (CDCl3, 400 MHz): δ=3.95 (s, 3 H), 7.01 (s, 1 H), 7.05 (dd, J=8.59, 1.77 Hz, 1 H).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionThe residue was diluted with EtOAc (15 mL)
3. washwashed with water (10 mL)
4. washwashed with brine (10 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto yield a yellow solid
9. customThe crude material was purified by silica gel chromatography on an ISCO combi-flash Rf system

ORD record

ord-ee2b719ee77c4f6a87db3d69fe0fe720

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096624B2