3-Bromoaniline → HCID 57516627, compound

Participants

Reaction Conditions

Reaction Steps

3-Bromophenylamine (10.0 g, 58.1 mmol) and 3,3-dimethyl-dihydro-furan-2,5-dione (8.2 g, 63.9 mmol) were suspended in 300 ml DCM. The reaction was stirred at 50° C. for 3 h. The reaction was cooled to room temperature and 1,1′-carbonyldiimidazole (11.3 g, 69.7 mmol) was added in portions. The reaction was heated again to 50° C. and stirred overnight. The solvent was evaporated and the product was crystallized from isopropyl alcohol to give 9.3 g of 1-(3-bromophenyl)-3,3-dimethyl-pyrrolidine-2,5-dione. The mother liquor was concentrated and chromatographed using a gradient of 0% to 20% ethyl acetate in hexanes to give another 1.3 g of product for a combined yield of 10.6 g (65%).

Provenance & Evidence