Sodium Hydroxide → HCID 178519455, compound

HRID 2404473Notes

Reaction equation

HRID 2404473 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[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([NH2:21])[CH:15]=1.[OH-].[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([C:9]2[NH:20][C:17]3[CH:18]=[CH:19][C:14]([F:13])=[CH:15][C:16]=3[N:21]=2)[OH:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 1645844-Fluorobenzene-1,2-diamineHCID 27570282-(3-Bromophenyl)-2-hydroxyacetic acid

Product 1

HCID 178519455HCID 178519455, compound

Procedure

A mixture of (3-bromophenyl)hydroxyacetic acid (3.7 g) and 4-fluoro-ortho-phenylenediamine (2 g) in 5N aqueous hydrochloric solution (3.2 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 chromatography over silica gel (gradient dichloromethane/methanol/ammonia from 98/2/0.5 to 90/10/0.5) to afford the pure 3-bromophenyl(5-fluoro-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 chromatography over silica gel (gradient dichloromethane/methanol/ammonia from 98/2/0.5 to 90/10/0.5)

Sources & evidence

ORD record
ord-0ce76f00e8fe49b89f7c3d4ab7862c0f
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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