Potassium Carbonate → 5-Bromobenzofuran-2-yl pyrid-3-yl ketone

HRID 280624Notes

Reaction equation

HRID 280624 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.Br.Br[CH2:13][C:14]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([C:14]([C:13]2[O:10][C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=3[CH:7]=2)=[O:15])[CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 27762343-(2-Bromoacetyl)pyridine hydrobromide

Product 1

HCID 233209425-Bromobenzofuran-2-yl pyrid-3-yl ketoneYield 72.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 5-bromosalicylaldehyde (17.7 g), 3-bromoacetylpyridine hydrobromide (25.3 g) and anhydrous potassium carbonate (60.8 g), in 2-butanone (200 ml) was heated under reflux with stirring for 5 hours. The mixture was filtered and the solid was washed with 2-butanone. The combined filtrate and washings were evaporated and the residue was crystallised from methanol to give 5-bromobenzofuran-2-yl pyrid-3-yl ketone (19.2 g), m.p. 144°-145°.

Workup

  1. temperatureunder reflux
  2. filtrationThe mixture was filtered
  3. washthe solid was washed with 2-butanone
  4. customThe combined filtrate and washings were evaporated
  5. customthe residue was crystallised from methanol

Sources & evidence

ORD record
ord-8eaa3f5fe909402888ea44219a2a5e1a
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

Loading…