Di-tert-butyl azodicarboxylate → HCID 90315915, compound

Participants

Reaction Steps

Isopropylmagnesium chloride-lithium chloride complex (1.3 M in THF, 21.8 mL, 28.3 mmol) was added dropwise to a cold (−78° C.) solution of 3-bromo-4-methoxybenzonitrile (5 g, 23.6 mmol) in THF (100 mL), under argon. The reaction mixture was allowed to warm to rt. Di-tertbutyl azodicarboxylate (5.43 g, 23.58 mmol) was added. The reaction mixture was stirred for 3 h at rt, diluted with a saturated aqueous solution of ammonium chloride (175 mL), and extracted with EtOAc. The organic layers were combined, washed with a saturated solution of sodium bicarbonate, dried (Na2SO4), and concentrated. The residue was purified by silica gel column chromatography (hexane/EtOAc, 95:5→7:3) to provide 5.5 g of the title compound. tR: 1.16 min (LC-MS 4); ESI-MS: 362.2 [M−H]− (LC-MS 4); Rf=0.55 (hexane/EtOAc, 1:1).

Provenance & Evidence