These common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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. SDS of cas: 59247-47-1
4-[4-(4-carboxyphenyl)-piperazin-1-yl]-benzoic acid tert-butyl ester To a degassed mixture of 4-(piperazin-1-yl)-benzoic acid ethyl ester (1.45g, 6.2 mmol), 4-bromobenzoic acid tert-butyl ester (1.75g, 6.8 mmol), cesium carbonate (3.9g, 12 mmol) in dioxane (25 mL) was added tris(dibenzylideneacetone)dipalladium (300 mg, 5 molpercent) and 2-(dicyclohexylphosphino)-2′,4′,6′-tris(isopropyl)-biphenyl (x-phos, 300 mg, 10 molpercent). The mixture was heated in a sealed tube with stirring at 100 ¡ãC for 3 hrs. Solvents were evaporated and the residue was extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate and solvents were evaporated. The crude material was purified through a flash column chromatography using ethyl acetate and hexanes to give the intermediate 4-[4-(4-ethoxycarbonylphenyl)-piperazin-1-yl]-benzoic acid tert-butyl ester as solid (1.3 g, 51 percent yield) The above intermediate, (1.2g, 2.68 mmol) was suspended in methanol (100 mL) and THF (100 mL) and sodium hydroxide solution (1N, 80 mL) was added. The mixture was refluxed for 2 hrs and then concentrated. The mixture was acidified with 1N HCl and the solid formed was filtered to give 4-[4-(4-carboxyphenyl)-piperazin-1-yl]-benzoic acid tert-butyl ester (1.1g). LCMS calcd for C22H26N204 (m/e) 382. Obsd: 381 (M-H+)
The synthetic route of tert-Butyl 4-bromobenzoate has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Madrigal Pharmaceuticals, Inc.; BOLIN, David, R.; CHEUNG, Adrian, Wai-hing; HAMILTON, Matthew, Michael; MARCOPULOUS, Nicholas; McDERMOTT, Lee, Apostle; QIAN, Yimin; EP2350311; (2013); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics