4-Bromophenol → HCID 66727956, compound

HRID 573284Notes

Reaction equation

HRID 573284 reaction equation
CS([C:5]1[NH:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[N:6]=1)(=O)=O.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.[OH-].[Na+]>>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:5]2[NH:9][C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[N:6]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 78084-BromophenolHCID 14798Sodium HydroxideHCID 3035262-(methylsulfonyl)-1H-benzimidazole

Product 1

HCID 66727956HCID 66727956, compoundYield 69.9%

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(methylsulfonyl)-1H-benzo[d]imidazole (5.6 g), 4-bromophenol (24.69 g) and TEA (19.89 mL) was stirred at 120° C. for 15 h. The mixture was added with 8 M NaOH aqueous solution and extracted with AcOEt. The organic layer was separated, washed with water and brine, dried over Na2SO4 and concentrated under reduced pressure. The precipitate was collected by filtration to give the first lot of the titled compound (5.77 g). The filtrate was evaporated, and the precipitate was collected by filtration to give the second lot of the titled compound (0.92 g).

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-22a242e1bcd944bf8f4430a46ed2052b
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

Loading…