Potassium Carbonate → HCID 86697218, compound

HRID 237552Notes

Reaction equation

HRID 237552 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].Br[CH:12]1[CH2:16][CH2:15][N:14]([CH3:17])[C:13]1=[O:18].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH:12]2[CH2:16][CH2:15][N:14]([CH3:17])[C:13]2=[O:18])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 111829543-Bromo-1-methylpyrrolidin-2-one

Product 1

HCID 86697218HCID 86697218, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-3,5-dimethylphenol (100 mg) in N,N-dimethylformamide (2 mL) is added 3-bromo-1-methylpyrrolidin-2-one (100 mg) and K2CO3 (105 mg). The mixture is stirred for 12 hours at room temperature. Then the mixture is partitioned between water and diethylether. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→50:50) to give the title compound. Yield: 65 mg; LC (method 7): tR=1.0 min; Mass spectrum (ESI+): m/z=298 [M+H]+.

Workup

  1. customThen the mixture is partitioned between water and diethylether
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→50:50)

Sources & evidence

ORD record
ord-e9e8c9c3040d4ed78c35abd9e13ca709
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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