Water → 2-Fluoro-3-methylaniline

Temperature

85 °C

6-Bromo-2-fluoro-3-methylaniline (9.00 g, 44.1 mmol), which had been obtained in Reference example 6 (6a), was dissolved in 1:1 mixture (130 mL) of N,N-dimethyl formamide and methanol, and added with [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride-dichloromethane complex (10.8 g, 13.2 mmol) and N,N-diisopropylethylamine (23 mL, 132.3 mmol). The mixture was vigorously stirred at 85° C. for 2 hours under a carbon monoxide atmosphere. The reaction solution was cooled to room temperature, added with ethyl acetate and water, filtered using Millicup (registered trademark)-LH, and washed with ethyl acetate. The filtered solution was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=4/1) to give the title compound as a colorless solid (5.70 g, yield 71%).

1. temperatureThe reaction solution was cooled to room temperature
2. filtrationfiltered
3. washwashed with ethyl acetate
4. extractionThe filtered solution was extracted with ethyl acetate
5. washThe organic layer was washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationThe solvent was distilled off under reduced pressure
8. customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=4/1)

ORD record

ord-6cc13dba6cfb45ee8616d09862cb870d

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173631B2