1-Fluoronaphthalene → 1-(4'-Fluoronaphth-1-yl)-3-methylbutan-1-one

HRID 33577

Reaction equation

HRID 33577 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:16](Cl)(=[O:21])[CH2:17][CH:18]([CH3:20])[CH3:19]>ClCCl>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:16](=[O:21])[CH2:17][CH:18]([CH3:20])[CH3:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 94501-FluoronaphthaleneHCID 66054Isovaleryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 597968761-(4'-Fluoronaphth-1-yl)-3-methylbutan-1-oneYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To an ice/salt cooled solution of 1-fluoronaphthalene (5.1 g) in anhydrous dichloromethane (20 ml) was added aluminium chloride (5.6 g). After 5 minutes, a solution of isovaleryl chloride (4.2 g) in anhydrous dichloromethane (5 ml) was added dropwise over 20 minutes. The mixture was allowed to warm to room temperature overnight, then added cautiously to a vigorously stirred mixture of ice water and dichloromethane. The organic layer was separated, clarified with methanol, washed with brine, dried with sodium sulphate, filtered and evaporated in vacuo. The title compound (7 g) was obtained following silica gel column chromatography of the residue in 20-40% dichloromethane in petroleum ether.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried with sodium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-039a8b57ca6e4078848737513c84cff0
Source dataset
uspto-grants-2008_09
Patent number
US07429607B2

Linked notes

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