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Structure of 875815-03-5

Chemical Structure| 875815-03-5

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Product Details of [ 875815-03-5 ]

CAS No. :875815-03-5
Formula : C9H8Br2O
M.W : 291.97
SMILES Code : O=C(C1=CC=CC(C)=C1)C(Br)Br

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Application In Synthesis of [ 875815-03-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 875815-03-5 ]

[ 875815-03-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 585-74-0 ]
  • [ 875815-03-5 ]
  • [ 51012-64-7 ]
YieldReaction ConditionsOperation in experiment
93% With N-Bromosuccinimide; silica gel; In methanol; for 0.25h;Reflux; General procedure: The alpha-bromination reaction was carried out using acetophenone (1200 mg, 10 mmol), N-bromosuccinimide (2136 mg, 12 mmol), 10% (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 Na2SO4, filtered and concentrated. The obtained crude product was purified by column chromatography over silica gel (60-120 mesh) using n-hexane-EtOAc (99:1 ratio). With the aim of studying the recycling of the catalyst, the isolated catalyst was washed with ethyl acetate (5mL) after its filtration from the reaction medium, collected and dried in vacuum at 70C to a constant weight. Subsequently it was reused for the alpha-bromination of acetophenone and achieved 95%, 86% and 83% yields of product (2a) for first, second and third reuse of catalyst respectively. All products gave spectroscopic data in agreement with the literature [15,21,27-30]. The method is also very practical for scale up in process development. We attempted large scale (100 gram scale) synthesis of 2-bromo-1-phenylethanone 2a and obtained fruitful results with isolated yields ranging from 93% to 96%.
  • 2
  • [ 875815-03-5 ]
  • [ 51012-64-7 ]
YieldReaction ConditionsOperation in experiment
170 mg With water; sodium sulfite; In ethyl acetate; acetone; at 20℃; General procedure: To a stirred solution of alkyne (1 mmol) in ethyl acetate(1 mL), 0.1 mL of acetone:water (1:1) and TsNBr2 (2 mmol) wasadded. After 10 min Na2SO3 (8 mmol) was added and the reaction was stirred at room temperature till completion asmonitored by TLC. The organic layer was extracted with ethylacetate, washed with water, dried with Na2SO4 and concentrated.The crude product was purified by flash chromatographyon silica gel (230-400 mesh) using petroleum ethereethyl acetateas eluent.
 

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