Application of 3972-64-3, A common heterocyclic compound, 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene, molecular formula is C10H13Br, 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.
A 1. 6 M solution of”butyllithium (0.85 mL, 1.36 mmol) was added to a solution of dicyclohexylamine (0.27 mL, 1.36 mmol) in toluene (5 mL). After stirring for 5 min, a mixture of cisltrans isomers of 3-methyl-cyclohexanecarboxylic acid 2- trimethylsilanyl-ethyl ester (269 mg, 1.11 mmol) was added. After stirring for 30 min, 1-bromo-3-tert-butyl-benzene (250 mg, 1.17 mmol) was added followed by the simultaneous addition of tri-tert-butylphosphonium tetrafluoroborate (31 mg, 107 pmol) and tris (dibenzylideneacetone) dipalladium (0)-chloroform adduct (54 mg, 52.2 pmol). The solution was placed into a preheated oil bath at 60 °C. After stirring for 20 h, the solution was diluted with 10percent aqueous hydrochloric acid, and extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was flash chromatographed with 49: 1,24 : 1, and 23: 2 hexanes: ethyl acetate as the eluant to yield 250 mg (62percent yield) of a mixture of cisltrans isomers of 1- (3-tert-butyl-phenyl)- 3-methyl-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester as a yellow oil. Method [2] Retention time 3.64 min by HPLC and 3.68 min by MS (M+Na=397).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/70407; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary