Iodine → HCID 68211900, compound

Participants

Reaction Steps

A mixture of 1-bromo-2-(bromomethyl)benzene (4.40 g, 17.60 mmol), magnesium (0.984 g, 40.5 mmol), and I2 (2.2 mg, 8.80 μmol) in Et2O (87 mL) was heated to reflux under argon until the reaction initiated (indicated by decolorization of I2) and then stirred at room temperature for 2 hours. After this time, the reaction mixture was added to a solution of tert-butyl 4-acetylpiperidine-1-carboxylate (2 g, 8.80 mmol) in Et2O (1.2 mL) and then stirred for 19 hours. At the conclusion of this period, the reaction mixture was quenched with aqueous NH4Cl (saturated, 20 mL) and extracted with EtOAc (3×25 mL). The combined organic layers were washed with H2O (3×15 mL) and brine (15 mL). The resulted organic layer was separated, dried (Na2SO4), filtered, and concentrated to yield a residue. The residue was purified by column chromatography (silica gel, hexanes/EtOAc gradient 0 to 60% EtOAc) to afford Compound 11A as a white semi-solid (1.14 g, 31% yield).

Provenance & Evidence