Chlorosuccinimide → 2-Butyl-4-chloro-5-methoxy-1-indanone

HRID 7854

Reaction equation

HRID 7854 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH2:9]([CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:22][CH3:23])[CH:19]=2)[C:14]1=[O:24])[CH2:10][CH2:11][CH3:12]>CN(C)C=O.CCOC(C)=O>[CH2:9]([CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:22][CH3:23])[C:19]=2[Cl:1])[C:14]1=[O:24])[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 120457522-Butyl-5-methoxy-1-indanone

Product 1

HCID 219909172-Butyl-4-chloro-5-methoxy-1-indanoneYield 15.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Chlorosuccinimide (505 mg, 3.8 mmol) was added to a solution of 2-butyl-5-methoxy-1-indanone (825 mg, 3.8 mmol) in anhydrous dimethylformamide (3.8 mL) and the resulting solution was stirred under nitrogen and at room temperature overnight. The reaction mixture was diluted with EtOAc (50 mL), washed with 5% aqueous NaHCO3 (20 ml), water (3×50 mL) and brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by column chromatography on EM silica gel 60 (2320-400 mesh, 2.75×29 cm), eluting with CH2Cl2, to afford 2-butyl-4-chloro-5-methoxy-1-indanone (148 mg) as an oil.

Workup

  1. washwashed with 5% aqueous NaHCO3 (20 ml), water (3×50 mL) and brine (10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe residue was purified by column chromatography on EM silica gel 60 (2320-400 mesh, 2.75×29 cm)
  6. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-4ea1ea522fe849c09b6b48ecf0c1b923
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Linked notes

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