Cesium carbonate → 1-(2-(4-Bromo-3,5-dimethylphenoxy)ethyl)pyrrolidin-2-one

HRID 237480Notes

Reaction equation

C([O-])([O-])=O.[Cs+].[Cs+].CC1C=CC(S([O:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][C:21]2=[O:25])(=O)=O)=CC=1.[Br:26][C:27]1[C:32]([CH3:33])=[CH:31][C:30](O)=[CH:29][C:28]=1[CH3:35]>CN(C)C=O>[Br:26][C:27]1[C:32]([CH3:33])=[CH:31][C:30]([O:17][CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][C:21]2=[O:25])=[CH:29][C:28]=1[CH3:35]

Participants

Conditions

Temperature: 50 °C

Procedure

Cs2CO3 (850 mg) is added to a solution of 2-(2-oxopyrrolidin-1-yl)ethyl 4-methylbenzenesulfonate (390 mg) and 4-bromo-3,5-dimethylphenol (200 mg) in N,N-dimethylformamide (4 mL). The mixture is heated to 50° C. for 12 hours and partitioned between diethylether and saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (ethyl acetate) to give the title compound. Yield: 210 mg; Mass spectrum (ESI+): m/z=312 [M+H]+.

Workup

custompartitioned between diethylether and saturated aqueous NH4Cl solution
dry with materialThe organic phase is dried (MgSO4)
concentrationconcentrated
customThe residue is chromatographed on silica gel (ethyl acetate)

Sources & evidence

ORD record: ord-ab759291a5c144e28f17fe20b160ada6
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642585B2

Reaction notes

Loading…