N,N'-Dimethylethylenediamine → 1-(4-Bromophenyl)pyrrolidin-2-one

The mixture of pyrrolidin-2-one (1.3 g, 15 mmol), 1-bromo-4-iodobenzene (2.8 g, 9.8 mmol), copper iodide (0.19 g, 0.98 mmol), cesium fluoride (3.7 g, 25 mmol) and N,N′-dimethylethylenediamine (186 mg, 0.196 mmol) in 1,4-dioxane (100 mL) was evacuated and back-filled with nitrogen three times. The reaction mixture was stirred at room temperature for 48 hours. The mixture was filtered and the filtrate was concentrated to give a white solid. The solid was purified by combi flash silica gel chromatography to give the title compound (1.1 g, 46% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.52 (d, 2H), 7.48 (d, 2H), 3.83 (t, 2H), 2.59 (t, 2H), 2.18 (m, 2H).

1. customwas evacuated
2. additionback-filled with nitrogen three times
3. filtrationThe mixture was filtered
4. concentrationthe filtrate was concentrated
5. customto give a white solid
6. customThe solid was purified by combi flash silica gel chromatography

ORD record

ord-f74b59aa582e438399f99e9698dc00fc

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394285B2