Acetic Anhydride → 1-(3-bromophenyl)-1H-pyrrole-2,5-dione

HRID 1677547Notes

Reaction equation

[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[Br:8][C:9]1[CH:10]=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=1.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>CCOCC.O>[Br:8][C:9]1[CH:10]=[C:11]([N:15]2[C:4](=[O:5])[CH:3]=[CH:2][C:1]2=[O:7])[CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

additionvia slow drop-wise addition
temperatureThe material was cooled to ambient and then in an ice bath
filtrationthe resultant precipitate was collected by filtration
washThe precipitate was washed with several volumes of water and finally with hexane (30 ml)
customThe material was dried over night in the vacuum oven

Sources & evidence

ORD record: ord-b19d05010a5d4dff84987a5d41edfee1
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008298B2

Reaction notes

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