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

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

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.