2,6-Dibromotoluene → 1-(3-Bromo-2-methylphenyl)-3-m-tolylimidazolidin-2-one

HRID 661864Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH3:9].[C:10]1([CH3:22])[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[CH2:20][CH2:19][NH:18][C:17]2=[O:21])[CH:11]=1.N[C@@H]1CCCC[C@H]1N>O1CCOCC1.[Cu]I>[Br:8][C:4]1[C:3]([CH3:9])=[C:2]([N:18]2[CH2:19][CH2:20][N:16]([C:12]3[CH:11]=[C:10]([CH3:22])[CH:15]=[CH:14][CH:13]=3)[C:17]2=[O:21])[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of 1,3-dibromo-2-methylbenzene (185 mg, 0.740 mmol), 1-m-tolylimidazolidin-2-one (50 mg, 0.284 mmol), copper (I) iodide (5.40 mg, 0.028 mmol), tripotassium phophosphate (120 mg, 0.567 mmol) and (+/−trans-1,2-diaminocyclohexane (3.4 μL, 0.028 mmol) in 1,4-dioxane (1 mL) was purged with nitrogen and heated at 120° C. in a sealed tube. After 21.5 h, the mixture was concentrated and the residue was purified by column chromatography (eluting with a gradient from hexane to 50:50 hexane-EtOAc) to provide 1-(3-bromo-2-methylphenyl)-3-m-tolylimidazolidin-2-one as a white solid (70 mg, 70%). 1H NMR (400 MHz, chloroform-d) δ 7.51-7.54 (1H, m), 7.49 (1H, s), 7.34 (1H, dd, J=8.05, 1.94 Hz), 7.24 (2H, d, J=8.05 Hz), 7.11 (1H, t, J=7.91 Hz), 6.90 (1H, d, J=7.49 Hz), 3.98-4.04 (2H, m), 3.81-3.87 (2H, m), 2.38 (3H, s), 2.36 (3H, s). Mass spectrum m/z 345, 347 (M+H)+.

Workup

concentrationthe mixture was concentrated
customthe residue was purified by column chromatography (
washeluting with a gradient from hexane to 50:50 hexane-EtOAc)

Sources & evidence

ORD record: ord-2f332e4f05fc46b9b8190486ef91bbd5
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084620B2

Reaction notes

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