33786-89-9

14862-52-3

33786-89-9

The general procedure for the synthesis of 5-chlorobenzene-1,3-diamine from 1,3-dibromo-5-chlorobenzene is as follows: Example 3 General Method C: To aryl halide (2.0 mmol) was added Pd2(dba)3 (37 mg, 0.04 mmol, 2 mol%), 2-(dicyclohexylphosphino)biphenyl (34 mg, 0.1 mmol, 4.8 mol%), LiHMDS (803 mg, 4.8 mmol, 2.4 eq.) and 4 mL of toluene. The reaction mixture was stirred at room temperature for 17 hours. Upon completion of the reaction, the reaction mixture was quenched with 1N HCl (5 mL) and stirring was continued for 5 min at room temperature. Subsequently, the mixture was alkalized to pH=12 with 1N NaOH and the layers were separated. The organic layer was concentrated. Synthesis of 5-chlorobenzene-1,3-diamine was carried out by general method C using 5-chloro-1,3-dibromobenzene (540 mg, 2.0 mmol) as feedstock. The brown oily product was isolated in 97% yield (299 mg, 105% recovery, 83% purity). 1H NMR (400 MHz, CDCl3): δ 6.10 (s, 2H), 5.87 (s, 1H), 3.60 (br s, 4H); 13C NMR (100 MHz, CDCl3): δ 148.3, 135.5, 105.9, 99.7; HRMS calculated value C6H8N2Cl (M + H) 143.0370, measured value 143.0369.