4-Cyanophenacyl bromide

off-white to light yellow crystalline powder

In a 100 mL round bottom flask, 10 mmol of 4-cyanoacetophenone and 11 mmol of N-bromosuccinimide (NBS) were added.35mL of ethyl acetate dissolved, Then add 1g of Amberlyst 15 ion exchange resin as catalyst.The reaction was warmed to 40°C and reacted. After TLC tracks the reaction, The reaction solution was filtered to remove Amberlyst 15 ion exchange resin, The filtrate was spin-dried and separated by column chromatography (eluent: petroleum ether/ethyl acetate) to give a white solid with a yield of 61percent.In a 100 mL round bottom flask, 10 mmol of 4-cyanoacetophenone and 11 mmol of N-bromosuccinimide (NBS) were added.35mL of ethyl acetate dissolved, Then add 1g of Amberlyst 15 ion exchange resin as catalyst.The reaction was warmed to 40°C and reacted. After TLC tracks the reaction, The reaction solution was filtered to remove Amberlyst 15 ion exchange resin, and the filtrate was spin-dried.Column chromatography (eluent: petroleum ether/ethyl acetate) afforded a white solid in 61percent yield.General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NHj) g) General procedure: A mixture of haloalkyne (0.2 mmol), tetrafluoroboric acid (20 molpercent, 40percent  aqueous solution ) in 2, 2, 2-trifluoroethanol (1 mL) was stirred at 80°C for 2 or 10 h. After the reaction was finished, water (5 mL) was added and the solution was extracted with ethyl acetate (3×5 mL), the combined extract was dried with anhydrous MgSOGeneral 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.General 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 NaThe reactor was charged with 2.5 mL of 1, 2-dichloroethane, AlCl3 (0.55 g, 4.14 mmol), 2-bromoacetyl bromide (1.21 g g, 6.0 mmol) was added dropwise at 0 ° C, followed by the dropwise addition of benzonitrile (0.52 g, 5.0 mmol) at one time. After the addition was complete, the cooling was stopped and stirring was continued for 4 h, the temperature was raised to room temperature, the deionized water was added to quench the excess of AlCl3, The organic layer was separated and evaporated to dryness, and the crude product was purified by column chromatography to give Compound 1-1 (0.9g, 80 percent).General procedure: Oxone (1.352 g, 2.2 mmol) was added to the well stirred solution of substrate (2 mmol) and NH

4-(2-Bromoacetyl)benzonitrile is useful for the irreversible inhibitory activity of Glycogen synthase kinase 3 (GSK-3). Phenylhalomethylketones can be used in the study of novel GSK-3 inhibitors.

Molecular Weight:224.05
XLogP3:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:222.96328
Monoisotopic Mass:222.96328
Topological Polar Surface Area:40.9
Heavy Atom Count:12
Complexity:210
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes