Cesium carbonate → 1-(3-bromophenyl)pyrrolidin-2-one

HRID 1677366Notes

Reaction equation

HRID 1677366 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](I)[CH:9]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20]>CS(C)=O.[Cu]Br>[Br:7][C:8]1[CH:9]=[C:10]([N:15]2[CH2:19][CH2:18][CH2:17][C:16]2=[O:20])[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 120252-Pyrrolidone

Product 1

HCID 8996681-(3-bromophenyl)pyrrolidin-2-oneYield 57.9%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a flask charged with Cs2CO3 (4.74 g), Copper(I) bromide (99 mg), and ethyl-2-cyclohexanone-carboxylate (248 mg) was added 3 mL of DMSO under an argon atmosphere. 1-bromo-3-iodobenzene (2.0 g) was added followed by a solution of 2-pyrrolidinone (715 mg) in 3 mL of DMSO. The reaction mixture was stirred at rt for 16 h and then heated to 90° C. for 24 h. The mixture was filtered over celite, concentrated and purified by flash chromatography (65:35 hexanes:ethyl acetate) to afford 983 mg of 1-(3-Bromo-phenyl)-pyrrolidin-2-one as a brown solid.

Workup

  1. temperatureheated to 90° C. for 24 h
  2. filtrationThe mixture was filtered over celite,
  3. concentrationconcentrated
  4. custompurified by flash chromatography (65:35 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-d385712d649f47c2bc6dbce0af6a1464
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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