1-(3-bromophenyl)-1H-pyrrole-2,5-dione → HCID 59540573, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 1-(3-bromo-phenyl)-pyrrole-2,5-dione (800 mg, 3.17 mmol) and bromo-trimethylsilanyl-trimethylsilanylmethylsulfanyl-methane (1.36 g, 4.76 mmol, [literature compound)) in dry DMF (3 ml) under nitrogen atmosphere. The material was heated at 110° C. (oil bath) for 2 hours and then cooled to ambient. The solvent was stripped (rotovap/pump) and the remainder taken up in benzene (30 ml) and brine (30 ml). The material was shaken and the organic phase collected. The aqueous phase was back-extracted with benzene (2×20 ml) and the organic phases combined, dried (MgSO4), filtered and stripped. The crude was purified by chromatography on silica gel eluting with 5% to 40% EtOAc in hexanes, providing 1.04 g of (3S,3aS,6aR)-5-(3-bromo-phenyl)-3-trimethylsilanyl-tetrahydro-thieno[3,4-c]pyrrole-4,6-dione as a light white-yellow solid.

Provenance & Evidence