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

HRID 572885Notes

Reaction equation

HRID 572885 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-697fe51aa7314b00ac31c501d4258ef9
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

Loading…