4-Bromophenol → HCID 123668110, compound

HRID 573317Notes

Reaction equation

HRID 573317 reaction equation
Cl[C:2]1[N:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]=1.[CH:17]1[C:22]([OH:23])=[CH:21][CH:20]=[C:19]([Br:24])[CH:18]=1>>[CH2:11]([O:10][C:8](=[O:9])[CH2:7][N:6]1[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[N:3]=[C:2]1[O:23][C:22]1[CH:21]=[CH:20][C:19]([Br:24])=[CH:18][CH:17]=1)[CH3:12]

Participants

3

Reactant 2

HCID 78084-BromophenolHCID 41591541-(ethoxycarbonylmethyl)-2-chlorobenzimidazole

Product 1

HCID 123668110HCID 123668110, compoundYield 63.6%

Conditions

Temperature
120 °C

Procedure

To a mixture of ethyl 2-(2-chloro-1H-benzo[d]imidazol-1-yl)acetate (11.0 g) and p-bromophenol (23.9 g) was added TEA (19.2 mL) at room temperature. After stirring overnight at 120° C., the reaction mixture was quenched with water and extracted with AcOEt. The organic layer was separated, washed with 1 M NaOH aqueous solution and brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (AcOEt/hexane) and recrystallized from AcOEt/hexane to give the title compound (11.0 g).

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with AcOEt
  3. customThe organic layer was separated
  4. washwashed with 1 M NaOH aqueous solution and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (AcOEt/hexane)
  8. customrecrystallized from AcOEt/hexane

Sources & evidence

ORD record
ord-b2be0f4a6f56413f89a23406d7a8edaf
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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