Boron tribromide → 4-[3-(4-Hydroxy-phenyl)-propyl]-3-methyl-1-(4-trifluoromethyl-benzyl)-imidazolidin-2-one

HRID 1985250Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH:12]2[CH2:16][N:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[C:14](=[O:28])[N:13]2[CH3:29])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl.O>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH:12]2[CH2:16][N:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[C:14](=[O:28])[N:13]2[CH3:29])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-[3-(4-methoxy-phenyl)-propyl]-3-methyl-1-(4-trifluoromethyl-benzyl)-imidazolidin-2-one (3.51 g, 8.63 mmol) in dry CH2Cl2 (60 mL), cooled to −78° C. and then treated dropwise with BBr3 (6.49 g, 25.9 mmol). The reaction was warmed 0° C. and stirred for 2 h under N2. The reaction mixture was diluted with water and extracted with CH2Cl2. The organic layer was dried (MgSO4), and the solvent removed in vacuo to give crude product that was purified by flash chromatography using 2:1 hexanes:acetone to afford 3.01 g (89%) 4-[3-(4-hydroxy-phenyl)-propyl]-3-methyl-1-(4-trifluoromethyl-benzyl)-imidazolidin-2-one. 1H NMR. MS (ES30) Calc'd for C21H24N2O2F3 (M+1) 393. Found m/z 393 (100%).

Workup

extractionextracted with CH2Cl2
dry with materialThe organic layer was dried (MgSO4)
customthe solvent removed in vacuo
customto give crude product that
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-8369fe1e28404e279101e4ad5f5b8fb9
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544812B2

Reaction notes

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