4-Bromophenol → 2-(4-Bromophenoxy)-1-methyl-1H-benzo[d]imidazole

HRID 587560Notes

Reaction equation

HRID 587560 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[CH:12]1[C:17]([OH:18])=[CH:16][CH:15]=[C:14]([Br:19])[CH:13]=1>C(N(CC)CC)C>[Br:19][C:14]1[CH:15]=[CH:16][C:17]([O:18][C:2]2[N:6]([CH3:7])[C:5]3[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=3[N:3]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 78084-BromophenolHCID 6630802-chloro-1-methyl-1H-1,3-benzodiazole

Product 1

HCID 585774542-(4-Bromophenoxy)-1-methyl-1H-benzo[d]imidazoleYield 24.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
120 °C

Procedure

Triethylamine (18 mL) was added to a mixture of 2-chloro-1-methyl-1H-benzimidazole (7.2 g) and p-bromophenol (22.5 g) at room temperature. The mixture was stirred at 120° C. for 6 h. The mixture was quenched with water at room temperature and extracted with EtOAc. The organic layer was separated, washed with 1 N NaOH aq. and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 10%-15% EtOAc in hexane) to give 2-(4-bromophenoxy)-1-methyl-1H-benzimidazole (3.2 g) as colorless crystals.

Workup

  1. customThe mixture was quenched with water at room temperature
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with 1 N NaOH aq. and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (NH silica gel, eluted with 10%-15% EtOAc in hexane)

Sources & evidence

ORD record
ord-f2a7556579ac4ebea39590ca57484cd9
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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