Yield:13132-28-0 11.95 g

Reaction Conditions:

with Nitryl chloride in tetrachloromethane at 0; for 0.5 h;

Steps:

Commercially available acenaphthylene (31.58 g, 75% purity, 0.156 mol) was dissolved in carbon tetrachloride (100 mL) and cooled to 0 C. A solution of NO2Cl (9.8 g, 0.12 mol) in carbon tetrachloride (100 g) was added dropwise to the stirred acenaphthylene solution while maintaining the temperature at 0 C. After the addition was complete, stirring was continued for a further 30 min. The solution was washed with 5% aqueous sodium bicarbonate solution (250 mL) and water (250 mL) and the aqueous solutions were back extracted with chloroform to minimize losses. The combined organic solutions were dried over sodium sulfate, filtered, and the solvents removed under reduced pressure. The solid residue was dissolved in a small amount of toluene, loaded onto a silica column, and eluted with hexanes. The first yellow fraction was discarded, and the product was then collected as an orange fraction. Evaporation of the solvent gave 1- nitroacenaphthylene (11.95 g, 60.6 mmol, 50%) as an orange powder, mp 122e123 C (lit. mp [45] 124e125 C). 1 H NMR (500 MHz, CDCl3): d 8.40 (1H, d, J 7.0 Hz, 8-H), 8.10 (dd, 1H, J 8.0, 0.6 Hz), 8.03 (s, 1H, 2-H), 8.01 (d, 1H, J 7.0 Hz, 3-H), 7.97 (d, 1H, J 8.2 Hz), 7.71e7.67 (m, 2H, 4,7-H). 13C (125 MHz, CDCl3): d 149.1, 132.9, 132.8, 131.5, 130.6, 130.1, 129.8, 128.8, 128.7, 128.6, 128.1, 126.7.

References:

Lash, Timothy D.;Rauen, Patrick J. [Tetrahedron,2021,vol. 100,art. no. 132481]