Simple exploration of 1,3-Dibromo-5-fluorobenzene

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.

1435-51-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1435-51-4, name is 1,3-Dibromo-5-fluorobenzene, A new synthetic method of this compound is introduced below.

A mixture of Pd(OAc)2 (88 mg, 0.394 mmol) and BINAP (294 mg, 0.473 mmol) in dioxane (8 mL) was stirred in a sealed tube for ~5 min. To the mixture was then added l,3-dibromo-5- fluorobenzene (0.496 mL, 3.94 mmol) and (tetrahydro-2H-pyran-4-yl)methanaminehydrochloride (299 mg, 1.969 mmol), stirring was continued for additional ~5 min and KOtBu (486 mg, 4.33 mmol) was added. The resulting mixture was heated at 93 C for ~18 hrs. The reaction mixture was cooled to room temperature, diluted with EtOAc (-50 mL) and MeOH (-10 mL), filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel, 40 g, EtO Ac/heptane = 5/95 to 30/70] providing 3-bromo-5-fluoro- N-((tetrahydro-2H-pyran-4-yl)methyl)aniline (220 mg) as a colorless liquid. LCMS (m/z): 289.9 [M+H]+; Retention time = 1.03 min.

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; NOVARTIS AG; ANTONIOS-MCCREA, William R.; BARSANTI, Paul A.; HU, Cheng; JIN, Xianming; MARTIN, Eric J.; PAN, Yue; PFISTER, Keith B.; SENDZIK, Martin; SUTTON, James; WAN, Lifeng; WO2012/66065; (2012); A1;,
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