Chlorosuccinimide → 6'-Bromo-5'-chlorospiro[cyclopentane-1,3'-indolin]-2'-one

HRID 2096958

Reaction equation

HRID 2096958 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[C:15](=[O:19])[NH:16]2)=[CH:12][CH:11]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:9][C:10]1[CH:18]=[C:17]2[C:13]([C:14]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[C:15](=[O:19])[NH:16]2)=[CH:12][C:11]=1[Cl:1]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 127170906'-Bromospiro[cyclopentane-1,3'-indolin]-2'-one

Product 1

HCID 669540836'-Bromo-5'-chlorospiro[cyclopentane-1,3'-indolin]-2'-oneYield 75.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-Chlorosuccinimide (500 mg, 3.75 mmol) was added to a solution of 6′-bromospiro[cyclopentane-1,3′-indolin]-2′-one (preparation 2, 0.20 g, 0.75 mmol) in chloroform (5 mL). The mixture was stirred and heated to reflux. After 6 hours, the mixture was cooled to room temperature. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction and the mixture was extracted with chloroform. The organic layer was washed with brine, dried (MgSO4) and evaporated. Purification of the residue by flash chromatography (8:2 hexanes/ethyl acetate) gave the title compound (0.17 g, 75%) as a white solid.

Workup

  1. temperatureheated to reflux
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customPurification of the residue by flash chromatography (8:2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-d0b2244179b040ddb63a7492cb8ec924
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Linked notes

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