5-Bromo-2-Chloroacetophenone

Pyridinium dichromate (2.6g, 6.94 mmol) was added to a solution of 1- (5-BROMO-2-CHLORO- phenyl)-ethanol (1.09 g, 4.6 mmol) in CH2CI2 (20 mL). The reaction was stirred for 15 hours and then more pyridinium dichromate (2.6g, 6.94 mmol) was added. After another 24 hours celite was added and the mixture was stirred for 20 mins. The reaction mixture was filtered through a pad of celite washing with ether. The filtrate was concentrated to a brown oil. The residue was purified by flash silica gel chromatography (0percent to 10percent EtOAc in hexanes) to give the title compound as a clear oil (0.92 G, 85percent). 1H NMR (400 MHz, CDC13) : 6 2.64 (s, 3H), 7.29 (d, J=8.6 Hz, 1 H), 7.51 (dd, J=8.6, 2.3 Hz, 1 H), 7.66 (d, J=2.3 Hz, 1 H).Pyridinium dichromate (2.6 g, 6.94 mmol) was added to a solution of 1-(5-bromo-2-chloro-phenyl)-ethanol (1.09 g, 4.6 mmol) in CHTo a stirred suspension of Methyltriphenylphosphonium bromide (26.8g, 75.l0mmol) in THF (50mL) was added n-butyl lithium (2.0M in hexane) (37.5mL, 75.l0mmol) at 0C. The reaction mixture was stirred for 5 min at 0C and l-(5-bromo-2-chlorophenyl)ethan-l- one (Step-2) (7.0g, 30.04mmol) in THF (50mL) was added at 0C and stirred for l6h at RT. After completion of reaction, it was quenched by 1N HC1 and extracted with diethyl ether. The ether layer was dried and concentrated to obtain the crude compound. The crude compound was purified by combiflash silica gel column (hexanes/EtOAc=95/5) to get the title compound (5.0g, 71.42%). This compound was taken for further step without purification.To a stirred solution of 5-bromo-2-chloro-N-methoxy-N-methylbenzamide (Step-l) (l l.Og, 39.49mmol) in THF (lOOmL) was added methyl magnesium bromide (3.0M in THF) (l9.7mL, 59.24 mmol) at 0C under inert atmosphere and stirred for l6h at RT. After completion of reaction, it was quenched by 1N HC1 and extracted with diethyl ether. The ether layer was dried and concentrated and purified by combiflash silica gel column(hexanes/EtOAc=95/5) to obtain the title compound (7.0g, 76.0%). LCMS: m/z = Not ionized. The product obtained was taken to the next step without purification.

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