Boron tribromide → HCID 68869787, compound

HRID 1985227Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[CH3:30])[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=2)[N:8]([CH2:23][CH2:24][CH3:25])[C:7]1=[O:26].B(Br)(Br)Br>C(Cl)Cl.CCOCC>[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[CH3:30])[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)[N:8]([CH2:23][CH2:24][CH3:25])[C:7]1=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

A 0° C. solution of 1-(3,4-dimethyl-benzyl)-4-[3-(4-methoxy-phenyl)-propyl]-5-methyl-3-propyl-1,3-dihydro-imidazol-2-one (0.145 g, 0.357 mmol) in CH2Cl2 (6 mL) was treated dropwise with BBr3 (0.10 mL, 1.06 mmol) and then stirred at 0° C. under N2 for 30 minutes. The reaction was diluted with Et2O and then quenched with ice and then water. The organic layer was dried (MgSO4), and the solvent removed in vacuo to afford 0.169 g (100%) 1-(3,4-dimethyl-benzyl)-4-[3-(4-hydroxy-phenyl)-propyl]-5-methyl-3-propyl-1,3-dihydro-imidazol-2-one that was utilized without purification.

Workup

customquenched with ice
dry with materialThe organic layer was dried (MgSO4)
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-140baa4757b5429f9050d31a9c8b9150
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544812B2

Reaction notes

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