Water → HCID 22916376, compound

HRID 265380Notes

Reaction equation

HRID 265380 reaction equation
B(Br)(Br)Br.[CH2:5]([O:7][C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[C:21]([C:22]2[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=2)=[C:20]([C:30]2[CH:35]=[CH:34][C:33]([O:36]C)=[CH:32][CH:31]=2)[N:19]=[CH:18]1)=[O:9])[CH3:6].O>ClCCl>[CH2:5]([O:7][C:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[C:21]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[C:20]([C:30]2[CH:31]=[CH:32][C:33]([OH:36])=[CH:34][CH:35]=2)[N:19]=[CH:18]1)=[O:9])[CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 22916350HCID 22916350, compound

Product 1

HCID 22916376HCID 22916376, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1.3 ml) was added to a solution of 1-(7-ethoxycarbonylheptyl)-4,5-bis(4-methoxyphenyl)-imidazole (1.25 g) in dry dichloromethane (30 ml). The reaction was stirred at room temperature for 4 h, cooled and water (20 ml) was carefully added. The resulting purple precipitate was collected and column chromatography on silica gel eluted with a dichloromethane:methanol gradient, followed by recrystallisation from ethanol and water gave 1-(7-ethoxycarbonylheptyl)-4,5-bis(4-hydroxyphenyl)-imidazole as a white solid (0.58 g, 50%), m.p. 186°-187°.

Workup

  1. temperaturecooled
  2. customThe resulting purple precipitate was collected
  3. washcolumn chromatography on silica gel eluted with a dichloromethane
  4. custommethanol gradient, followed by recrystallisation from ethanol and water

Sources & evidence

ORD record
ord-3b97847f93ef4f61aacfa258c3dee744
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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