3-fluoro-N-(2-fluorophenyl)-2-nitroaniline → 3-fluoro-N1-(2-fluorophenyl)benzene-1,2-diamine

To 2-fluoroaniline (1.55 g, 13.9 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (0.56 g, 13.9 mmol) and the reaction stirred for 10 minutes prior to the addition of 2,6-difluoronitrobenzene (2 g, 15.5 mmol) dissolved in anhydrous dimethylformamide (2 mL). Upon disappearance of 2-fluoroaniline the reaction was partitioned between saturated ammonium chloride (50 mL) and ethyl acetate (50 mL) and the organics were dried over sodium sulfate. The product was purified on silica gel using the ISCO (0-70% ethyl acetate/hexane) to give (3-Fluoro-2-nitro-phenyl)-(2-fluoro-phenyl)-amine as a slightly impure off-white solid (1.5 g, 43%). (3-Fluoro-2-nitro-phenyl)-(2-fluoro-phenyl)-amine (1.5 g, 6 mmol) and a spatula tip of 5% Pd/C in methanol (100 mL) were reduced in the parr shaker. Upon complete reduction, the reaction was filtered through a pad of celite and concentrated onto silica gel. The product was purified on silica gel using the ISCO (0-70% ethyl acetate/hexane) to give 3-fluoro-N1-(2-fluorophenyl)benzene-1,2-diamine as a brown oil (0.5 g, 38%). MS (ES) m/z 221.1

1. filtrationUpon complete reduction, the reaction was filtered through a pad of celite
2. concentrationconcentrated onto silica gel
3. customThe product was purified on silica gel using the ISCO (0-70% ethyl acetate/hexane)

ORD record

ord-d6843c5ec05f4cd890b1046fbf277188

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687529B2