Hydrochloric Acid → (5-Bromo-pyrimidine-2-yl)-phenyl-methanone

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Reaction Steps

5-Bromo-pyrimidine-2-carbonitrile (2.5 g, 13.59 mmol) is dissolved ether (30 mL), and PhMgBr (3 ether solution, 13.59 mmol, 4.53 mL) is added dropwise at rt. The mixture is heated to reflux for 3 h under N2, and then cooled to rt. THF (30 mL) is added followed by the addition of 2 N aqueous HCl (10 mL). The resulting solution is stirred at rt for 30 min, and water (30 mL) is added. The aqueous layer is extracted with EtOAc (3×20 mL). The combined organic layer is washed with saturated aqueous NaHCO3 (15 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting 70% EtOAc in heptane to afford (5-bromo-pyrimidine-2-yl)-phenyl-methanone (3.01 g, 84%) as a solid. MS: 264 (M+H).

Provenance & Evidence