1-(5-BROMO-2-FURYL)ETHANONE

To a solution of 2-acetylfuran (20 mmol) in DMF (20 mL) was added portionwise N-bromosuccinimide (22 mmol) with stirring. To a solution of 1 (10 g, 90 mmol) in DMF 40 mL, NBS (19g, 108 mmol) was added by keeping the temperature at 0 °C. Thereaction mixture was stirred overnight at room temperature. Upon completion, the reaction mixture was poured into ice-cold water. The mixture was dilutedwith EtOAc, and the insoluble material was filtered off through Celite. Theorganic layer of the filtrate was washed with brine, dried anhydrous magnesiumsulfate, and concentrated. The residue was chromatographed (SiO2, EtOAc/n-hexane, 1/19, v/v) to afford compound 2 (8.7 g, 45.4mmol, 50.4percent). Synthesis of 2-acetyl-5-bromofuran (29) Synthesis of 2-acetyl-5-bromofuran (29) To a stirred solution of compound 4 (5.0 g, 45.45 mmol) and DMF (50 mL), NBS (8.8 g, 50 mmol) was added portion-wise at room temperature under stirring. The reaction mixture was allowed to stir at room temperature overnight. 50percent starting material remained by TLC and LCMS. Reaction mixture was poured into cold water and the compound was extracted with diethyl ether (150 mL X 3). Combined organic layer was washed with brine, dried over sodium sulphate and concentrated under reduced pressure. Crude compound was purified by column chromatography using 5percent ethyl acetate in n-hexane as an eluent to afford compound 43 (2.4 g, 28percent) as a white solid.

Molecular Weight:189.01
XLogP3:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:187.94729
Monoisotopic Mass:187.94729
Topological Polar Surface Area:30.2
Heavy Atom Count:9
Complexity:124
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes