Benzene, 1-bromo-3-iodo- → 3-Bromo-N-[(oxan-4-yl)methyl]aniline

참여 물질

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Palladium (II) acetate (14.28 mg, 0.06 mmol) and racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (79 mg, 0.13 mmol) were suspended in toluene (3 mL). The mixture was evacuated and purged with nitrogen, and warmed to 50°C. In a separate vessel, 1-bromo-3-iodobenzene (240 mg, 0.85 mmol), (tetrahydro-2H-pyran-4-yl)methanamine (98 mg, 0.85 mmol) and sodium-t-butoxide (122 mg, 1.27 mmol) were suspended in toluene (3.5 mL). The resulting mixture was evacuated, purged with nitrogen and warmed to 50°C. After ~30 mins, the catalyst mixture was transferred to the reaction vessel. The reaction was evacuated and purged with nitrogen and heated at 80°C overnight. This reaction was combined with EN06953-06 for purification. The mixture was filtered and purified by flash silica chromatography, elution gradient 0 to 40% EtOAc in heptane. Pure fractions were evaporated to dryness to afford 3-bromo-N-((tetrahydro-2H-pyran-4-yl)methyl)aniline (71.0 mg, 31.0 %) as a colourless oil which crystallised on standing. The main impurity was isolated (EN06953-09-02) but this was not identified; assume it is BINAP or the catalyst- ligand complex.

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