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Chemistry
Organic Building Blocks
Aryls
Ethyl 3-(2,3-dichlorophenyl)-3-oxopropanoate
Chemistry
Organic Building Blocks
Aryls
Chlorides Esters Ketones Benzene Compounds

[ CAS No. 672323-07-8 ] {[proInfo.proName]}

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Chemical Structure| 672323-07-8
Chemical Structure| 672323-07-8
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Product Details of [ 672323-07-8 ]

CAS No. :672323-07-8 MDL No. :MFCD09756184
Formula : C11H10Cl2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 261.10 Pubchem ID :-
Synonyms :

Safety of [ 672323-07-8 ]

Signal Word: Class:
Precautionary Statements: UN#:
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Application In Synthesis of [ 672323-07-8 ]

* 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 [ 672323-07-8 ]

[ 672323-07-8 ] Synthesis Path-Downstream   1~3

YieldReaction ConditionsOperation in experiment
80%
80%
80%
  • 2
  • [ 672323-07-8 ]
  • [ 302-15-8 ]
  • 3-(2,3-dichlorophenyl)-1-methyl-1H-pyrazol-5-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
33.4% With triethylamine In ethanol at 25 - 80℃; for 2h; 57.2 57.2 3 -(2,3 -Dichlorophenyl)- 1-methyl- 1H-pyrazol-5-ol To a solution of methyldiazanediium sulfate (14.7 g, 0.103 mol) in ethanol (90 mL) andtriethylamine (19.2 mL, 0.138 mol) was added ethyl 3-(2,3-dichlorophenyl)-3-oxopropanoate (18 g,0.069 mol) as a solution in ethanol (90 mL) at a temperature of about 25°C. The reaction mixture was heated to 80°C for 2 hours, after which time TLC showed complete consumption of the startingmaterial. The solvent was removed under reduced pressure and the resulting slurry was added to water (150 mL) and extracted with ethyl acetate (2 x 150 mL). The organic layers were combined, washedwith brine (50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure toprovide the cyclised product, which was chromatographed by silica gel column chromatography eluting with 20-25% ethyl acetate:hexane (5.6g, 33.4% yield) ‘H NMR (400 MHz, DMSO) ppm: 11.13 (s,1H), 7.68 (dd, J=7.8, 1.6 Hz, 1H), 7.58 (dd, J=8.0, 1.6 Hz, 1H), 7.36 (t, J=7.9 Hz, 1H), 5.87 (s, 1H),3.59 (s, 3H).
Reference： [1]Current Patent Assignee: THE JOHNS HOPKINS UNIVERSITY; BRISTOL-MYERS SQUIBB CO - WO2015/183839, 2015, A1 Location in patent: Page/Page column 264
  • 3
  • [ 2905-60-4 ]
  • [ 141-78-6 ]
  • [ 672323-07-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethyl acetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 2,3-dichlorobenzoyl chloride In tetrahydrofuran; hexane at -70 - -65℃; for 0.5h; 57.1 57.1 Ethyl 3 -(2,3 -dichlorophenyl)-3 -oxopropanoate To a stirred solution of di-iso-propylamine (8.7 g, 0.086 mol) in THF (100 mL) cooled to-78°C was added n-BuLi (49.2 mL of a 1.6 M solution in hexanes, 0.079 mol). Stirring was continued for 30 minutes after which time, freshly distilled ethyl acetate (6.94 g, 0.079 mol) was added drop wise at -78°C. The resulting solution was stirred for 30 minutes whereupon 2,3 dichloro benzoyl chloride(15 g, 0.072 mol) was added as a solution in THF (150 mL). The reaction mixture was stirred at -65 to-70°C for 30 minutes and then terminated by the addition of 1 N HC1 solution (until acidic). Theresulting bi-phasic mixture was allowed to warm to a temperature of about 25°C before being diluted with ethyl acetate (250 mL) and the organic layer was collected. The aqueous layer was extracted with ethyl acetate (2 x 150 mL) and the organic layers were combined, washed with brine (30 mL), driedover sodium sulfate, filtered and concentrated under reduced pressure to provide the beta-keto ester which was used directly in the next step.
Reference： [1]Current Patent Assignee: THE JOHNS HOPKINS UNIVERSITY; BRISTOL-MYERS SQUIBB CO - WO2015/183839, 2015, A1 Location in patent: Page/Page column 264

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