4-Fluoro-1,2-phenylenediamine

White to brown powder

A solution of 5-fluoro-2-nitroaniline in MeOH (0.32 M) was added to Pd/C (5percentw/w, 10percentw). The reaction mixture was stirred at R.T.under HGeneral procedure: Nitro aromatic (1.0 mmol), B2(OH)4 (5.0 equiv, 5.0 mmol), and H2O (3.0 mL) were added in a10 mL tube. The reaction mixture was stirred at 80 °C for 8 h. When the reaction was completemonitored by TLC, the mixture was cooled to room temperature, extracted with ethyl acetate (3 ×20 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, andconcentrated under reduced pressure. The residue was purified by silica gel columnchromatography.General procedure: Nitrobenzene (0.6mmol), 5wtpercent Pd/C (0.5mmol percent, 0.003mmol), H2O (10 equiv, 6.0mmol), B2(OH)4 (3.3 equiv, 2.0mmol), and CH3CN (1.0mL) were added in a 10mL tube. The reaction mixture was stirred at 50°C for 24h. When the reaction was complete monitored by TLC, the mixture was cooled to room temperature. Water (5mL) was added, and extracted with EtOAc (3×5mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give aniline 2a (55mg, 99percent).4-fluoro-2-nitroaniline (8.00 g, 51.22 mmol) was dissolved in methanol (100 mL), and 10percent palladium-carbon powder (0.80 g) was added thereto, followed by stirring for four hours at room temperature under hydrogen atmosphere. When 5-fluoro-2-nitroaniline (4.496 g, 0.0288 mol) was dissolved in 150 ml of concentrated hydrochloric acid I turned it on. A small amount of tin (16.56 g, 0.140 mol) was added over 15 minutes at 0 . Room temperature Temperature), the mixture was stirred for 1 hour and then cooled overnight. Deionized water The mixture was poured into water and 4M sodium hydroxide (NaOH) was slowly added until pH 10 was reached. The organic layer was washed with Extracted with ethyl acetate (4 x 100 mL), washed with water (4 x 100 mL), dried over anhydrous magnesium sulfate 4). The solution was concentrated in vacuo to give 2.54 g of yellow

Molecular Weight:126.13
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:126.05932639
Monoisotopic Mass:126.05932639
Topological Polar Surface Area:52
Heavy Atom Count:9
Complexity:97.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes