6-BroMochroMan-2-one

A solution of bromine (155 ml) in dichloromethane (500 ml) was added during 30 min to a solution of 3, 4-dihydrocoumarin (450 g, 0.3 mol) in dichloromethane (2000 ml). The mixture was stirred overnight at 15°C, then diluted with dichloromethane (2000 ml), and washed with aqueous sodium bicarbonate (2 x 1000 ml) followed by water (1000 ml). The solution was dried over magnesium sulphate, filtered, and concentrated under reduced pressure. The residue was washed with petroleum ether (2 x 500 ml), and filtrate concentrated. The solid was recrystallised from dichloromethane/petroleum ether to give the bromide (BM1490) as thick white crystals (471 g, 74percent).Reference Example 13 [Step a] To a solution of compound 1 (5.00 g, 33.7 mmol) in dichloromethane (50.0 mL) was added dropwise a solution of bromine (1.80 mL, 35.4 mmol) in dichloromethane (20.0 mL) at room temperature, and the mixture was stirred for 7 hr. To the reaction solution was added water, and the mixture was extracted with chloroform. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The precipitated solid was suspended and washed in diisopropyl ether (10.0 mL), collected by filtration and washed with diisopropyl ether and hexane to give compound 2 (3.56 g, 46.5percent). MS(ESI)m/z: 227, 229(M+1)+.A solution of bromine (155 ml) in dichloromethane (500 ml) was added during 30 min to a solution of 3, 4-dihydrocoumarin (450 g, 0.3 mol) in dichloromethane (2000 ml). The mixture was stirred overnight at 15C, then diluted with dichloromethane (2000 ml), and washed with aqueous sodium bicarbonate (2 x 1000 ml) followed by water (1000 ml). The solution was dried over magnesium sulphate, filtered, and concentrated under reduced pressure. The residue was washed with petroleum ether (2 x 500 ml), and filtrate concentrated. The solid was recrystallised from dichloromethane/petroleum ether to give the bromide (BM1490) as thick white crystals (471 g, 74%).Reference [Step a] To a solution of compound 1 (5.00 g, 33.7 mmol) in dichloromethane (50.0 mL) was added dropwise a solution of bromine (1.80 mL, 35.4 mmol) in dichloromethane (20.0 mL) at room temperature, and the mixture was stirred for 7 hr. To the reaction solution was added water, and the mixture was extracted with chloroform. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The precipitated solid was suspended and washed in diisopropyl ether (10.0 mL), collected by filtration and washed with diisopropyl ether and hexane to give compound 2 (3.56 g, 46.5%). MS(ESI)m/z: 227, 229(M+1)+.a) 6-Bromochroman-2-oneTo a solution of 3, 4-dihydrocoumarin (3 mL, 24 mmol) in chloroform (15 mL) was added a solution of bromine (1.23 mL, 24 mmol) in acetic acid (5 mL). The resulting dark orange solution was stirred at room temperature for 16 h and turned EPO To a mixture of compound 6B (3.41 g, 14.956mmol) in THF at 0 was added CH3MgBr (32.9 mmol) . The mixture was allowed to stir at 020 for 16 hours, and then the mixture was quenched with NH4Cl, and extracted with ethyl acetate. The organic extract was washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo. Tthe residue obtained was purified using flash column chromatography (petroleum ether: ethyl acetate 20: 15: 1) to provide compound 6C.

Molecular Weight:227.05
XLogP3:2.3
Hydrogen Bond Acceptor Count:2
Exact Mass:225.96294
Monoisotopic Mass:225.96294
Topological Polar Surface Area:26.3
Heavy Atom Count:12
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes