1-(3-溴苯基)-1H-吡咯-2,5-二酮

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 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. cooled the organic phase collected The aqueous phase was back-extracted with benzene (2×20 ml) dried (MgSO4) filtered The crude was purified by chromatography on silica gel eluting with 5% to 40% EtOAc in hexanes

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of maleic anhydride (1.71 g, 17.4 mmol) in dry ether (25 ml) was added a solution of 3-bromo-phenylamine (3.0 g, 17.4 mmol) in ether (5 ml), via slow drop-wise addition. The material was stirred for 1 hour at ambient Sodium acetate (721 mg, 8.8 mmol) and then acetic anhydride (6 ml, 63 mmol) were added and the mixture was heated for 2 hours (oil bath, 100° C.). The material was cooled to ambient and then in an ice bath. Water (50 ml) was added with vigorous stirring and the resultant precipitate was collected by filtration. The precipitate was washed with several volumes of water and finally with hexane (30 ml). The material was dried over night in the vacuum oven to afford 2.84 g of 1-(3-bromo-phenyl)-pyrrole-2,5-dione as a light yellow-white powder. via slow drop-wise addition The material was cooled to ambient and then in an ice bath the resultant precipitate was collected by filtration The precipitate was washed with several volumes of water and finally with hexane (30 ml) The material was dried over night in the vacuum oven