2-Acetylpyridine → HCID 11833055, compound

HRID 919182Notes

Reaction equation

HRID 919182 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)(=[O:12])[CH3:11].C[O-].[Na+]>C(O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:11]/[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 142862-AcetylpyridineHCID 707414-BromobenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 11833055HCID 11833055, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol (500 mL) solution of 25.3 g (137 mmol) of 4-bromobenzaldehyde, 15.6 mL (139 mmol) of 2-acetylpyridine and 25.3 g of sodium methoxide (28% methanol solution, 131 mmol) were added under argon atmosphere, and the mixture was stirred at room temperature for 8 h. A formed solid was collected by filtration and washed with methanol to obtain 13.1 g (yield: 33%) of (E)-3-(4-bromophenyl)-1(2-pyridyl)-2-propen-1-one as a white solid.

Workup

  1. filtrationA formed solid was collected by filtration
  2. washwashed with methanol

Sources & evidence

ORD record
ord-7c3fa7f5b8f24101891efae593d1fb2a
Source dataset
uspto-grants-2016_03
Patent number
US09273002B2

Reaction notes

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