Fluorobenzene → (4-Fluorophenyl)(pyridin-3-yl)methanone

HRID 568080

Reaction equation

HRID 568080 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)=[O:9])=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 10008FluorobenzeneHCID 14798Sodium HydroxideHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 6451240Aluminum(III) Chloride

Product 1

HCID 762660(4-Fluorophenyl)(pyridin-3-yl)methanone

Conditions

Temperature
0 °C

Procedure

To a suspension of 140 g of nicotinic acid chloride hydrochloride in 500 ml of fluorobenzene cooled to 0° C. are added 280 g of aluminium chloride portionwise. The mixture is held under reflux for 6 hours, cooled and then poured onto ice. After the addition of sodium hydroxide up to pH=8, the mixture is extracted with dichloromethane. The organic phase is dried over magnesium sulphate and then evaporated under vacuum. The residue crystallises in a pentane/diisopropyl ether mixture giving 108.5 g of 3-(4-fluorobenzoyl)pyridine in the form of crystals melting at 91° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperaturecooled
  3. additionpoured onto ice
  4. extractionthe mixture is extracted with dichloromethane
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. customevaporated under vacuum
  7. customThe residue crystallises in a pentane/diisopropyl ether mixture

Sources & evidence

ORD record
ord-ffe533d9ce28413ca8cbdc337e853fb3
Source dataset
uspto-grants-2001_01
Patent number
US06180651B2

Linked notes

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