2-bromo-4-ethylacetophenone

Preparation of 2-bromo-1-(4-ethylphenyl)ethanone (Chem. Abstr. Reg. No. 2632- 14-6); 4'-ethylacetophenone (9 mL, 60 mmol) was dissolved in 100 mL anhydrous tetrahydrofuran, cooled to 0°C, then added phenyltrimethylammonium tribromide (22.6 g, 60 mmol) in portions. A precipitate slowly forms. The reaction mixture was stirred at 0General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NHGeneral procedure: The α-bromination reaction was carried out using acetophenone (1200 mg, 10 mmol), N-bromosuccinimide (2136 mg, 12 mmol), 10percent (w/w) silica gel (120mg) in 10 mL of methanol at reflux conditions until the disappearance of the substrate. (Note: 2136mg of N-bromosuccinimide was added portion wise i.e. 356 mg for each time in six portions). The progress of the reaction was monitored by TLC. The reaction mass was filtered after the completion of the reaction as per TLC and the catalyst was collected for reuse. The filtrate was concentrated under vacuum. Double distilled water was added to the reaction mixture and quenched with aqueous sodium thiosulfate and the product extracted with dichloromethane (Caution: Severe burning sensation of eyes was observed during the work-up process). The layers were separated and the organic layer was collected and washed thrice with distilled water (3×50mL). The collected organic layer was dried over anhydrous NaGeneral procedure: A mixture of haloalkyne (0.5 mmol), AgF (5molpercent) and water (1 equiv.) in TFA (1 mL) was stirred at 40°C for 6h, after which TFA was distilled out for reuse. The residue was separated by column chromatography to give the pure sample.

Molecular Weight:227.10
XLogP3:3.2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:225.99933
Monoisotopic Mass:225.99933
Topological Polar Surface Area:17.1
Heavy Atom Count:12
Complexity:148
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes