Ethyl Acetate → 2-Chloro-5-(4-fluorobenzoyl)pyridine

HRID 2110987Notes

Reaction equation

HRID 2110987 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][N:7]=1.CCOC(C)=O.[OH-].[Na+].[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[Cl:5][C:6]1[N:7]=[CH:8][C:9]([C:10]([C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)=[O:11])=[CH:13][CH:14]=1

Participants

6

Reactant 5

HCID 8857Ethyl AcetateHCID 10008Fluorobenzene2×HCID 14798Sodium HydroxideHCID 27821656-Chloronicotinoyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 226266762-Chloro-5-(4-fluorobenzoyl)pyridine

Conditions

Temperature
80 °C

Procedure

Aluminium chloride (2 g) was suspended in 3 ml of fluorobenzene. A solution of 6-chloronicotinoyl chloride (1 g, 5.7 mmol) in 2 ml of fluorobenzene was added to the stirred reaction mixture by syringe and stirred at 80° C. overnight in a closed vial. The reaction mixture was deluted with EtOAc and basified with aqueous sodium hydroxide (pH>8.5). The precipitate formed was removed by filtration. The organic solution was washed with water, dried over magnesium sulfate and concentrated by rotary evaporation. Desired product was purified by column chromatography on silica (EtOAc/hexane) to give 1.22 g (90%).

Workup

  1. customThe precipitate formed
  2. customwas removed by filtration
  3. washThe organic solution was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated by rotary evaporation
  6. customDesired product was purified by column chromatography on silica (EtOAc/hexane)
  7. customto give 1.22 g (90%)

Sources & evidence

ORD record
ord-93e7e7faa5334bb68f2745dbc2da66f6
Source dataset
uspto-grants-2009_04
Patent number
US07517992B2

Reaction notes

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