2-(2-Bromopyridin-3-yl)-1-(3-chlorophenyl)ethanol → 2-(2-Bromopyridin-3-yl)-1-(3-chlorophenyl)ethanone

HRID 1027689Notes

Reaction equation

HRID 1027689 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Br:12][C:13]1[C:18]([CH2:19][CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[OH:21])=[CH:17][CH:16]=[CH:15][N:14]=1>ClCCl>[Br:12][C:13]1[C:18]([CH2:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)=[O:21])=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

4

Reactant 2

HCID 581389372-(2-Bromopyridin-3-yl)-1-(3-chlorophenyl)ethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 581389712-(2-Bromopyridin-3-yl)-1-(3-chlorophenyl)ethanoneYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a vigorously stirred solution of pyridinium chlorochromate and celite in dichloromethane (20 mL) at room temperature was added a solution of 2-(2-bromopyridin-3-yl)-1-(3-chlorophenyl)ethanol in dichloromethane (10 mL). The mixture was stirred at room temperature for 3 hours then filtered through a plug of silica gel, eluted well with dichloromethane and concentrated in vacuo. Purification by chromatography on silica gel gave 2-(2-bromopyridin-3-yl)-1-(3-chlorophenyl)ethanone (313 mg, 64% yield) as white solid.

Workup

  1. filtrationthen filtered through a plug of silica gel
  2. washeluted well with dichloromethane
  3. concentrationconcentrated in vacuo
  4. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-83c80895a4d047f0b02b6e434afe40ae
Source dataset
uspto-grants-2014_05
Patent number
US08735399B2

Reaction notes

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