Dichloromethane → 2'-Chloro-5-nitro-3-trifluoromethyl-biphenyl-4-ylamine

Participants

Reaction Conditions

Reaction Steps

4-Bromo-2-nitro-6-trifluoromethyl-phenylamine (1.01 g, 3.55 mmol), 2-chlorophenylboronic acid (1.5 eq., 833 mg, 5.33 mmol), and (dppf)PdCl2.DCM (0.05 eq., 145 mg, 0.178 mmol) were placed in a 40 mL vial equipped with a magnetic stir bar. The vial was evacuated and backflushed with Ar, and DME (15 mL) and 2M aq Na2 CO3 (5 mL) were added via syringe. The vial was capped tightly and placed in a heating block where the reaction was stirred at 90° C. for 18 h. The mixture was cooled to rt, diluted with EtOAc, and washed with water. The aqueous layers were combined and extracted with EtOAc. The combined organic extracts were dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using a 24-g SiO2 pre-packed column eluting with EtOAc/hexanes, 0 to 1:4, v/v over 20 min, yielding 1.05 g (94%) of the desired compound. 1H-NMR (400 MHz, CDCl3) δ: 8.47 (d, J=2.0 Hz, 1H), 7.89 (d, J=2.0 Hz, 1H), 7.47-7.53 (m, 1H), 7.30-7.37 (m, 3H), 6.76 (br. s., 2H).

Provenance & Evidence