1,3-Dibromo-2-propanone → 2-Pyridinyloxymethyl ketone

HRID 225955

Reaction equation

HRID 225955 reaction equation
Br[CH2:2][C:3]([CH2:5]Br)=[O:4].[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1>C1C=CC=CC=1>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[O:7][CH2:2][C:3]([CH2:5][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 699521,3-Dibromo-2-propanoneHCID 178516071HCID 178516071, compound

Product 1

HCID 688285572-Pyridinyloxymethyl ketoneYield 14%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The bromomethyl ketone derivative X (3.2 g, 7.93 mmol), an intermediate in Preparation 5, was dissolved in benzene (30 ml), Ag2CO3 (2.62 g, 1.2 Eq) and 2-hydroxypyridine (0.93 g, 1.2 Eq) were added, and the mixture was stirred under reflux at 80□ for 3 days. The reaction mixture was filtered through Celite, concentrated under reduced pressure, and purified by column chromatography to give 2-pyridinyloxymethyl ketone derivative (XIf) (466 mg, Yield 14%).

Workup

  1. temperatureunder reflux at 80□ for 3 days
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-40b7a2c9f7874a0a82b7c2f704f95c56
Source dataset
uspto-grants-2009_07
Patent number
US07557133B2

Linked notes

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