Reference of 7051-16-3,Some common heterocyclic compound, 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene, molecular formula is C8H9ClO2, 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.
A solution of 1-chloro-3,5-dimethoxybenzene (5 g, 29.0 mmol) and TMEDA (4.37 mL, 29.0 mmol) in diethyl ether (100 mL, 962 mmol) at -78 C under N2 atmosphere was charged with BuLi (19.91 mL, 31.9 mmol) dropwise over a period of 30 minutes using a syringe pump. After stirring for 4 hours at -78 C, DMF was added and the reaction mixture continued to stir for 1.5 hours after which 1N HCl (~30 mL) was added (all at -78 C). The reaction mixture was warmed to room temperature and extracted withy ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The residue was purified by ISCO using hexanes/EtOAc as eluent. Fractions containing the desired product were concentrated to dryness to give the title material (1.97 g, 9.82 mmol, 33.9% yield) as a light yellow solid. LC (Method B): 1.924 min. LCMS (APCI): calcd for C9H10ClO3 [M+H]+ m/z 201.03, found 201.0. 1H NMR (CDCl3, 400 MHz): delta ppm 10.28 (s, 1H), 6.87 (s, 2H), 3.86 (s, 6H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Chloro-3,5-dimethoxybenzene, its application will become more common.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; UNIVERSITE DE MONTREAL; PRIESTLEY, Eldon Scott; POSY, Shoshana L.; TREMBLAY, Francois Tremblay; MARTEL, Alain; MARINIER, Anne; WO2013/163241; (2013); A1;,
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