4-Bromophenol → HCID 66727956, compound

HRID 572159Notes

Reaction equation

HRID 572159 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(OCC)(=O)C>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[NH:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[N:3]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 8471TriethylamineHCID 785722-Chlorobenzimidazole

Product 1

HCID 66727956HCID 66727956, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloro-1H-benzimidazole (5.6 g), 4-bromophenol (9.87 g) and triethylamine (19.89 ml) was stirred at 120° C. for 15 hr, and ethyl acetate was added. The reaction mixture was washed with 1 M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. A solid precipitated from the residue was collected by filtration to give the title compound (5.77 g).

Workup

  1. washThe reaction mixture was washed with 1 M aqueous sodium hydroxide solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customA solid precipitated from the residue
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-69bc1928a65e4b52b7df0832f63bbe06
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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