Synthetic Route of 129316-09-2,Some common heterocyclic compound, 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene, molecular formula is C10H12Br2, 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.
Step 1: tert-Butyl 3-bromo-5-(tert-butyl)benzoate (11a) n-Butyl lithium (7.2 mL, 18.0 mmol, 2.5M in THF) was added to a 100 mL flask under nitrogen atmosphere containing 9 mL of toluene at -10C. n-Butylmagnesium chloride (4.5 mL, 9.0 mmol, 2M in THF) was then added at such a rate to keep the temperature below -5C. The resulting milky slurry was aged at -10C for 30 min. To this slurry was added 1,3-dibromo-5-(tert-butyl)benzene (6.2 g, 21.2 mmol) dissolved in 20 mL of toluene. The rate of addition was such that the temperature did not increase above -5C. After addition was complete, the mixture was kept at -10C until the metal-halogen reaction was complete. A solution of di-tert-butyl dicarbonate (5.89 g, 27 mmol) in 7.5 mL of toluene was then charged such at a rate to keep the temperature below -5C. After the addition was complete, the mixture was kept at -10C until the aryl-Mg intermediate was completely consumed. The mixture was quenched by the addition of 40 mL of a 10% (w/w) aqueous solution of citric acid, which resulted in an exothermic generation of carbon dioxide. The phases were separated and the organic layer was washed with another 40 mL of citric acid solution. The organic extracts were then dried with MgSO4 and the solvents were removed at reduced pressure. Compound 11c was obtained as a brown oil (4.0 g, 60%).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-5-(tert-butyl)benzene, its application will become more common.
Reference:
Patent; Phenex Pharmaceuticals AG; EP2511263; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary