1-(4-Bromo-3-chlorophenyl)ethanone

PREPARATION 13 To a stirred solution of 4-bromo-3-chloro-/V-methoxy-/V-methyl-benzamide (4.6 g, 17 mmol) in tetrahydrofuran was added 3.0 M solution of methyl magnesium bromide (6.6 ml, 20 mmol) slowly at 5 °C. The resultant reaction mixture was stirred at room temperature for 2.5 h. The reaction mixture was poured into 20percent aqueous HCI (300 ml.) and then extracted with EtOAc (3 x 150 mL). The combined organic layers were washed with brine (1 x 100 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography to give 3.0 g the 2-bromo-1 -(4-bromo-3-chloro- phenyl)ethanone .4-Bromo-3-chloro-N-methoxy-N-methyl-benzamide (115 g) was mixed in tetrahydrofuran (575 mL). To the reaction solution was added dropwise 1M methylmagnesium bromide/tetrahydrofuran solution (516 mL) under ice cooling, and the reaction solution was stirred for 2 hours under ice cooling. To the reaction solution was added dropwise 1M hydrochloric acid (550 mL) under ice cooling, and then to the mixture was added ethyl acetate (500 ml). The mixed solution was separated, and the aqueous layer was then extracted with ethyl acetate. The resulted organic layer was collected and washed sequentially with water and aqueous saturated sodium chloride solution, and dried over magnesium sulfate. After removing magnesium sulfate on a filter, the filtrate was concentrated under reduced pressure. To the resulted residue were added diisopropylether and hexane, and the precipitated solid was filtered to give the titled compound (91.5 g). (0648)

Molecular Weight:233.49
XLogP3:2.9
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:231.92906
Monoisotopic Mass:231.92906
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes