2,6-Dibromotoluene → 1-Benzyl-3-(3-bromo-2-methylphenyl)imidazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

Step 2 A mixture of 1,3-dibromo-2-methylbenzene (0.147 mL, 1.064 mmol), 1-benzylimidazolidin-2-one (75 mg, 0.426 mmol), copper (I) iodide (8.11 mg, 0.043 mmol), (+/−)-trans-1,2-diaminocyclohexane (5.1 mL, 0.043 mmol) and tripotassium phosphate (181 mg, 0.851 mmol) in dioxane (2 mL) was sonicated while bubbling with argon for 1 min. The mixture was heated in a sealed tube at 120° C. After 18.25 h, the mixture was cooled to rt, diluted with EtOAc and filtered through Celite. The filtrate was concentrated and the residue was purified by column chromatography (eluting with a gradient from 20:80 EtOAc-hexane to EtOAc) to provide 1-benzyl-3-(3-bromo-2-methylphenyl)imidazolidin-2-one as a waxy white solid (36 mg, 25%). 1H NMR (400 MHz, chloroform-d) δ 7.49 (1 H, dd, J=7.9, 0.9 Hz), 7.28-7.40 (5 H, m), 7.19 (1 H, dd, J=7.8, 1.0 Hz), 7.08 (1 H, t, J=7.9 Hz), 4.46 (2 H, s), 3.64 (2 H, dd, J=8.8, 6.8 Hz), 3.37 (2 H, dd, J=8.8, 7.0 Hz), 2.36 (3 H, s). Mass spectrum m/z 346.8 (M+H)+.

Provenance & Evidence