These common heterocyclic compound, 14862-52-3, name is 3,5-Dibromochlorobenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: chlorides-buliding-blocks
Example 3 General Procedure C To the aryl halide (2.0 mmol), Pd2(dba)3 (37 mg, 0.04 mmol, 2 mol %) and 2-(dicyclohexylphosphino)biphenyl (34 mg, 0.1 mmol, 4.8 mol %) were added LiHMDS (803 mg, 4.8 mmol, 2.4 equiv.) and 4 mL toluene. The reaction mixture was stirred at room temperature for 17 h. At reaction completion, the mixture was quenched with 1N HCl (5 mL) and stirred at room temperature for 5 min. Then, it was basified to pH=12 with 1N NaOH and the layers were separated. The organic layer was concentrated. 5-Chlorobenzene-1,3-diamine General Procedure C was followed using 5-chloro-1,3-dibromobenzene (540 mg, 2.0 mmol). The product was isolated as a brown oil in 97% yield (299 mg, 105% mass recovery and 83% purity). 1H NMR (400 MHz, CDCl3): delta 6.10 (s, 2 H), 5.87 (s, 1 H), 3.60 (br s, 4 H); 13C NMR (100 MHz, CDCl3): delta 148.3, 135.5, 105.9, 99.7; HRMS calcd for C6H8N2Cl (M+H) 143.0370, found 143.0369.
The synthetic route of 3,5-Dibromochlorobenzene has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Boehringer Ingelheim International, GmbH; US2006/258888; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics