Boron tribromide → HCID 57719312, compound

HRID 1985243Notes

Reaction equation

HRID 1985243 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]([CH3:24])=[CH:20][CH:19]=3)[C:14](=[O:25])[N:13]2[CH2:26][CH2:27][CH3:28])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl.CCOCC.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:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=3)[C:14](=[O:25])[N:13]2[CH2:26][CH2:27][CH3:28])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 25134Boron tribromideHCID 57719093HCID 57719093, compound

Product 1

HCID 57719312HCID 57719312, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-[3-(4-methoxy-phenyl)-propyl]-1-(4-methyl-benzyl)-3-propyl-imidazolidin-2-one (1.22 g, assume 3.21 mmol) was dissolved in dry CH2Cl2 (25 mL), cooled to 0° C. and then treated dropwise with BBr3 (2.41 g, 9.63 mmol). The reaction was stirred at 0° C. for 1 h. The reaction mixture was diluted with Et2O and water, the organic layer was dried (MgSO4), and the solvent removed in vacuo to give crude product that was purified by flash chromatography using 1:1 hexanes:EtOAc to afford 0.687 g (68%) 4-[3-(4-hydroxy-phenyl)-propyl]-1-(4-methyl-benzyl)-3-propyl-imidazolidin-2-one. MS (ES+) Calc'd for C23H31N2O2 (M+1) 367. Found m/z 367 (100%). 1H NMR.

Workup

  1. dry with materialthe organic layer was dried (MgSO4)
  2. customthe solvent removed in vacuo
  3. customto give crude product that
  4. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-9498a3b88cfa47cc94cb8c7694d0d06a
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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