1-(5-Bromo-2-methoxyphenyl)ethanone

General procedure: To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 molpercent, 0.02 mmol) and CHCompound 41-2 (0492) To a solution of 41-1 (2.0 g, 13.32 mmol) in acetone (25 mL) was added NBS (2.37 g, 13.32 mmol) and 1M HCl aq. (0.13 mL, 0.13 mmol). The reaction mixture was stirred at room temperature for 3 h, and then concentrated to dryness under reduced pressure. The residue was dissolved with PE (40 mL) the resultant precipitate was filtered and dried in vacuum to afford 41-2 as a white solid (2.90 g, yield: 95percent).1-(5-Bromo-2-methoxy-phenyl)-ethanone Potassium carbonate (9.6 g) was added to a solution of 1-(5-bromo-2-hydroxyphenyl)ethanone (4.98 g) in acetone (50 mL) and the suspension was stirred at rt for 1 h. Intermediate 7a) Potassium carbonate (9.6 g) was added to a solution of 1 -(5-bromo-2-hydroxyphenyl)ethanone (4.98 g) in acetone (50 mL) and the suspension was stirred at rt for 1 h. Methyl iodide (1.89 mL) was added and the reaction mixture was stirred at rt for 20 h at which time it was filtered and the volatiles were removed under reduced pressure. The residue was diluted in EtA mixture of 5-Bromo-2-hydroxyacetophenone 2a (10g, 46.5mmol, 1 eq), potassium carbonate (9.62g, 69.75mmol, 1.5 eq) and iodomethane (5.8mL, 93mmol, 2 eq) in DMF (120mL) were stirred overnight in a sealed round bottom flask at room temperature. DMF was removed under reduced pression and the residue was partitioned between water and EtOAc. The combined EtOAc extracts were washed with brine, 0.5M NaOH and then three times with water. The organic layer was dried over MgSOTo a stirred solution of 1 -(5-bromo-2-hydroxyphenyl)ethan- 1-one 1 (10 g, 46.51 mmol) in DMF (100 mL) were added K2C03 (9.63 g, 69.77 mmol) and Mel (5.8 mL, 93.02 mmol) at 0°C under Ar. The mixture was stirred at RT for 12 h then quenched with water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with brine (80 mL), dried over Na2 SO4, filtered and concentrated under reduced pressure to afford compound 2 (8.8 g, 75percent) as pale yellow liquid. ‘H NIVIR (500MHz, DMSO-d6): 7.70 (dd, J 9.0, 2.6 Hz, 1H), 7.64 (d, J= 2.6 Hz, 1H), 7.16 (d, J= 9.0 Hz, 1H), 3.88 (s, 3H), 2.52 (s, 3H); LC-MS (ESI):m/z 228.8 (M + Hf).

Molecular Weight:229.07
XLogP3:2.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:227.97859
Monoisotopic Mass:227.97859
Topological Polar Surface Area:26.3
Heavy Atom Count:12
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes