Morpholine → 3-bromo-4-morpholinofuran-2(5H)-one

HRID 446803Notes

Reaction equation

HRID 446803 reaction equation
[Br:1][C:2]1[C:3](=[O:8])[O:4][CH2:5][C:6]=1Br.C([O-])([O-])=O.[Cs+].[Cs+].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>CN(C=O)C>[Br:1][C:2]1[C:3](=[O:8])[O:4][CH2:5][C:6]=1[N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 1546383,4-Dibromo-2(5H)-furanone

Product 1

HCID 583680173-bromo-4-morpholinofuran-2(5H)-oneYield 87.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3,4-dibromofuran-2(5H)-one (1 g, 0.004 mol) in DMF (10 mL) was added Cs2CO3 (1.34 g, 0.004 mol) followed by morpholine (360 mg, 0.004 mol) at room temperature under a N2 atmosphere. The reaction mixture was then stirred for 30 minutes, quenched with ice water and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford 3-bromo-4-morpholinofuran-2(5H)-one (0.87 g, 85%) as a solid.

Workup

  1. customquenched with ice water
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12dd7f1936c64d1c9ee8584f18f117ef
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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