Boron tribromide → 1-(4-Hydroxyphenyl)-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

HRID 723337Notes

Reaction equation

HRID 723337 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[CH:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)[C:14]2=[O:31])=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH:17]=[CH:16][N:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)[C:14]2=[O:31])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 218733801-(4-Methoxyphenyl)-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

Product 1

HCID 218734101-(4-Hydroxyphenyl)-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (2.5 ml) was added to a solution of 1-(4-methoxyphenyl)-3-(4-phenoxyphenyl)-1,3-dihydroimidazol-2-one (6.0 g) in dichloromethane (75 ml) at 0° C. After 3 hours, saturated sodium bicarbonate solution was added and the organic phase was washed with saturated brine. The organic phase was dried over magnesium sulfate and concentrated, and the residue was purified by chromatography on silica gel (eluent: dichloromethane/methanol 9:1). The product with the molecular weight of 344.37 (C21H16N2O3); MS (ESI): 345 ([M+H]+), was obtained in this way.

Workup

  1. washthe organic phase was washed with saturated brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customthe residue was purified by chromatography on silica gel (eluent: dichloromethane/methanol 9:1)
  5. customMS (ESI): 345 ([M+H]+), was obtained in this way

Sources & evidence

ORD record
ord-11b1be71766849dbafc7ba1cf9aae1ff
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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