Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 74137-36-3, Quality Control of 1,3-Dibromo-5-methoxybenzene
General procedure: 2-Ethylhexyl 3-((3-bromo-5-methoxyphenyl)thio)propanoate was synthesised according to general procedures GP12 – from 1 ,3-dibromo-5-methoxybenzene (3.0 g, 1 1 .3 mmol), Pd2(dba)3 (0.25 mg, 2.5 mol%), Xantphos (0.32 mg, 5 mol%), 2-ethylhexyl-3-mercaptopropionate (1 .96 g, 9.02 mmol), DIPEA (4.15 ml_, 23.9 mmol) and toluene (30 ml_); 1 10 C, 8 h. Chromatography (12% EtOAc in hexane) afforded a pale orange solid (2.4 g, 66%). NMR (400 MHz, DMSO-c/6) delta 7.05 (t, J = 1 .6 Hz, 1 H), 6.99 (d, J = 2.0 Hz, 1 H), 6.87 (t, J = 2.0 Hz, 1 H), 3.95 (d, J = 5.6 Hz, 2H), 3.76 (s, 3H), 3.21 (t, J = 6.4 Hz, 2H), 2.63 (t, J = 6.8 Hz, 2H), 1 .52-1 .50 (m, 1 H), 1 .29-1 .24 (m, 8H), 0.87-0.82 (m, 6H). LCMS (ESI, -ve) m/z 217/219 (M-C11 H21O2)-. General procedures GP12 00690] Condition A – a mixture of bromide GP12_1 , Pd2(dba)3 (5 mol%), Xantphos (10 mol%), RSH (1 .0-1 .2 equiv.), NaO’Bu (1 .0-1 .2 equiv.) and ‘BuOH/toluene (1 :5) was degassed with argon and then stirred at 100 C for 16 h. After cooling to rt, the suspension was filtered through celite, washed with DCM and the solvent was removed under reduced pressure. Alternatively, the mixture was centrifuged at 2500 RPM for 5 minutes. The solution was decanted and concentrated under reduced pressure. The crude was purified by chromatography to afford sulfide GP12_2. (1128) [00691] Condition B – same as condition A, with DIPEA used instead of NaO’Bu and toluene used instead of ‘BuOH/toluene.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-methoxybenzene, and friends who are interested can also refer to it.
Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; SPRINGER, Caroline; MARAIS, Richard; NICULESCU-DUVAZ, Dan; LEUNG, Leo; SMITHEN, Deborah; CALLENS, Cedric; TANG, Haoran; (403 pag.)WO2017/141049; (2017); A1;,
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