Sodium Hydroxide → 3-bromophenyl(5,6-difluoro-1H-benzimidazol-2-yl)methanol

HRID 2404476Notes

Reaction equation

HRID 2404476 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:12])[C:9](O)=O)[CH:5]=[CH:6][CH:7]=1.[F:13][C:14]1[C:19]([F:20])=[CH:18][C:17]([NH2:21])=[C:16]([NH2:22])[CH:15]=1.[OH-].[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([C:9]2[NH:21][C:17]3[CH:18]=[C:19]([F:20])[C:14]([F:13])=[CH:15][C:16]=3[N:22]=2)[OH:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 27367551,2-Diamino-4,5-difluorobenzeneHCID 27570282-(3-Bromophenyl)-2-hydroxyacetic acid

Product 1

HCID 668357463-bromophenyl(5,6-difluoro-1H-benzimidazol-2-yl)methanol

Procedure

A mixture of (3-bromophenyl)hydroxyacetic acid (809 mg) and 4,5-difluoro-ortho-phenylenediamine (500 mg) in 5N aqueous hydrochloric solution (2 mL) is heated under reflux for 15 h and cooled back to room temperature. The mixture is basified with concentrated sodium hydroxide and extracted with ethyl acetate. The organic phase is then dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by trituration in dichloromethane to afford the pure 3-bromophenyl(5,6-difluoro-1H-benzimidazol-2-yl)methanol.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 15 h
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is then dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by trituration in dichloromethane

Sources & evidence

ORD record
ord-71b288e9bd9948c5a4d1d003f6b47148
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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