Ammonium Chloride → HCID 59315049, compound

Participants

Reaction Steps

Zinc (1.042 g, 15.93 mmol) was added to a mixture of tert-butyl 2-bromo-5-nitrobenzyl(methyl)carbamate (1 g, 2.90 mmol) and ammonium chloride (3.10 g, 57.9 mmol) in ethanol (10 mL). The mixture was stirred for 3 h at rt. The mixture was concentrated. Na2CO3 (sat., 50 mL) and EtOAc (50 mL) was added and stirred for 1 h. The phases were separated and the aqueous layer was extracted with EtOAc (2×50 mL). The organics were combined, washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography (loading in chloroform, 0% to 50% ethyl acetate in hexane over 30 min using a 40 g silica gel cartridge) to yield 12A (0.785 g, 2.490 mmol, 86% yield) as a yellow oil.

Provenance & Evidence