2,4-Dichlorophenacyl bromide

White to brown low melting solid

General procedure: N-bromosuccinimide (0.37 mmol) was added to the stirredsolution of acetophenone (2) (0.37 mol, 1 equiv) in acetonitrile(40 mL). The resulting reaction mixture was stirredfor 10–15 min. After that p-TsOH (0.74 mmol, 2 equiv) wasadded to the reaction mixture and refluxed for 4–5 h andmonitored by TLC. After completion of reaction, reactioncontent was brought to room temperature and washed withsaturated solution of sodium bicarbonate and extracted withethyl acetate (3 × 20 mL), organic layer was dried oversodium sulphate and concentrated under reduced pressure.The obtained residues were purified by column chromatographyusing silica 100–200 mesh size by ethyl acetate:hexane (4:96) mixture and pure compound was identified as2-bromo-1-phenyl-ethanone 3a–g.To a cold solution of 8 1 (10mmol) in 57 chloroform (25ml), 9 bromine (12mmol) in chloroform (10ml) was gradually added in 30min with continuous stirring. The temperature of the reaction mixture was maintained under 0°C. After the addition was complete, the reaction mixture was slowly heated to the room temperature, and stirred for another 60min until the evolution of hydrogen bromide gas ceased. The solvent was removed under reduced pressure, and the residue obtained was recrystallized from ethanol to afford the pure 58 phenacyl bromide. Yield: 88percent. Mp 29–30°C. 64.70 mmol) in 40 ml chloroform, bromine (3.33 ml, 64.7 mmol) in30 ml chloroform were added drop wise at ambient temperature.The mixture was stirred at room temperature for 2 h and waswashed with H2O and saturated Na2S2O3 solution. The organicphase was dried over Na2SO4, filtered and the solvent was removedin vacuum. The crude product, 2-bromo-1-(2, 4-dichlorophenyl)ethanone (2) was recrystallized from petroleum ether. Yield: 73percent.10mmol 2, 4-dichloroacetophenone is added to a 100mL round bottom flaskAnd 11mmol of N-bromosuccinimide (NBS), 35mL of ethyl acetate dissolved, Then add 1g of Amberlyst 15 ion exchange resin as catalyst.The reaction solution was warmed to 40°C to react. After TLC tracks the reaction, The reaction solution was filtered to remove Amberlyst 15 ion exchange resin, The filtrate was evaporated to dryness and column chromatography (eluent: petroleum ether/dichloromethane) gave a white solid.Yield 20percent.10mmol 2, 4-dichloroacetophenone is added to a 100mL round bottom flaskDissolve with 11mmol of N-bromosuccinimide (NBS) and 35mL of ethyl acetate.Then add 1g of Amberlyst 15 ion exchange resin as catalyst.The reaction solution was warmed to 40°C to react. After TLC tracks the reaction, The reaction solution was filtered to remove Amberlyst 15 ion exchange resin, The filtrate was spin-dried and purified by column chromatography (eluent: petroleum ether/dichloromethane) to give a white solid with a yield of 20percent.General procedure: In a Nalgene.(R). bottle, to acetophenone (2 mmol) in dichloromethane (10 mL), potassium nitrate (4 mmol) and chloro/bromotrimethylsilane (8 mmol) were added. The heterogeneous mixture was stirred vigorously at 60 °C (for chlorination) or room temperature (for bromination) until the reaction went to completion (monitored by

2-Bromo-2',4'-dichloroacetophenone is a metabolite of the insecticide Bromfenvinphos. It is also a useful intermediate in the preparation of substituted acetophenone derivatives.

Molecular Weight:267.93
XLogP3:3.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:265.89008
Monoisotopic Mass:265.89008
Topological Polar Surface Area:17.1
Heavy Atom Count:12
Complexity:174
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes