1,3-Dibromobenzene → 1-(3-bromophenyl)pyrrolidin-2-one

HRID 331038Notes

Reaction equation

HRID 331038 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[NH:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[O:14].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:8][C:4]1[CH:3]=[C:2]([N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 79271,3-DibromobenzeneHCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 8996681-(3-bromophenyl)pyrrolidin-2-oneYield 67.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirring solution of 1,3-dibromobenzene (3 g, 12.72 mmol) in 1,4-dioxane (100 mL) was added 2-pyrrolidinone (0.975 mL, 12.72 mmol), palladium(II) acetate (0.143 g, 0.636 mmol), xantphos (0.736 g, 1.272 mmol) and cesium carbonate (8.29 g, 25.4 mmol). The mixture was then heated at 100° C. overnight. The reaction mixture was diluted with ethyl acetate (100 mL). The organic phase was washed with water (100 mL). The organic phase was collected, and the aqueous phase further extracted with ethyl acetate (2×50 mL). The organic phases were combined, dried over MgSO4, filtered and removed solvent under vacuo. The residue was purified on silica gel, eluting with a gradient of 0-40% ethyl acetate in cyclohexane to give the title compound (2.06 g). LCMS (A): m/z (M+H)+ 240/242, C10H10BrNO requires 239/241 (acidic).

Workup

  1. washThe organic phase was washed with water (100 mL)
  2. customThe organic phase was collected
  3. extractionthe aqueous phase further extracted with ethyl acetate (2×50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customremoved solvent under vacuo
  7. customThe residue was purified on silica gel
  8. washeluting with a gradient of 0-40% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-f8600a5fd2ce4774b0cee164cce0efc2
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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