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

To a solution of A (3.8 g, 16.5 mmol) in DCM (100 mL) was added PCC (8.4 g, 33.0 mmol). The mixture was stirred for 16 hours at room temperature. The reaction was filtered and the filtrate was concentrated and purified by flash column chromatography on silica gel (petroleum ether/EtOAc 5:1) to give B (3.6 g, 95percent yield) as off-white solid: 1H NMR (300 MHz, CDC13) ö ppm 7.45 (d, 1H), 6.96 (d, 1H), 6.82 (dd, 1H), 4.38 (q, 2H), 3.80(1, 3H), 2.62 (s, 3H).General procedure: In an oven dried Schlenk tube, were added alcohol 1 (69.0–199.5 mg, 0.5 mmol), CuI (10 molpercent)and 1, 10-Phenanthroline (20 molpercent) and K3PO4 (2 mmol) followed by the addition of dioxane (2mL) at room temperature under open air atmosphere. The stirred reaction mixture was heated inan oil bath at 80 C for 7–48 h. Progress of the reaction was monitored by TLC till the reaction iscompleted. Then, the reaction mixture was cooled to room temperature, quenched with aqueousNH4Cl solution and then extracted with CH2Cl2 (3 10 mL). The organic layer was washed withsaturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent under reducedpressure and purification of the crude material by silica gel column chromatography (petroleumether/ethyl acetate) furnished the aldehyde/ketone 2 (61–97percent).Preparation of 1-(2-bromo-5-methoxy-phenyl)-ethanone (108): EPO To an ice cold solution of 8.75 g (35 mmol) 2-bromo-5-methoxy-benzoyl chloride in 40 mL toluene, 9.63 mL (19.25 mmol) of a 2M toluene solution of dimethylzinc was added under argon atmosphere (dimethylzinc is pyrophoric-contact with air should be avoided). To an ice cold solution of 8.75 g (35 mmol) 2-bromo-5-methoxy-benzoyl chloride in 40 rnL toluene, 9.63 rnL (19.25 mmol) of a 2M toluene solution of dimethylzinc was added under argon atmosphere (dimethylzinc is pyrophoric - contact with air should be avoided.). The ice bath was removed and the mixture slowly warmed up to room temperature. Once the reaction starts it proceeds rapidly resulting in a turbid solution. The reaction was complete in 30 minutes. It was then cooled back to 0 General procedure: To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 molpercent, 0.02 mmol) and CH

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