4-Bromophenol → HCID 66727956, compound

HRID 573337Notes

Reaction equation

HRID 573337 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>>[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

3

Reactant 2

HCID 78084-BromophenolHCID 785722-Chlorobenzimidazole

Product 1

HCID 66727956HCID 66727956, compoundYield 62.8%

Conditions

Temperature
150 °C

Procedure

A mixture of 2-chloro-1H-benzo[d]imidazole (10 g), 4-bromophenol (56.7 g) and TEA (45.5 mL) was stirred at 150° C. overnight. The mixture was quenched with water at room temperature and extracted with AcOEt. The extract was washed with 1 M NaOH aqueous solution, dried over Na2SO4, and concentrated under reduced pressure. The precipitate was crystallized from AcOEt/hexane to give the title compound (11.9 g).

Workup

  1. customThe mixture was quenched with water at room temperature
  2. extractionextracted with AcOEt
  3. washThe extract was washed with 1 M NaOH aqueous solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe precipitate was crystallized from AcOEt/hexane

Sources & evidence

ORD record
ord-acdc16a708a94f4fba4653768716c7ff
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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