ChemicalBook CAS DataBase List 2-(4-CHLOROPHENYL)INDANE-1,3-DIONE

2-(4-CHLOROPHENYL)INDANE-1,3-DIONE synthesis

9synthesis methods

Product Name:2-(4-CHLOROPHENYL)INDANE-1,3-DIONE
CAS Number:1146-99-2
Molecular formula:C15H9ClO2
Molecular Weight:256.68

618-32-6 Synthesis

618-32-6
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$39.00/5g

140-53-4
504 suppliers
$13.00/25g

1146-99-2
52 suppliers
$50.00/100mg

Yield: 96.3%

Reaction Conditions:

with 1,4-diaza-bicyclo[2.2.2]octane;bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II);trimethylphosphine(hexafluoroacetylacetonato)copper(I);1-butyl-3-methylimidazolium trifluoromethanesulfonimide salt;silver trifluoromethanesulfonate in ethylene glycol;dimethyl sulfoxide at 90; for 2 h;Inert atmosphere;Reagent/catalyst;

Steps:

3
At room temperature, the appropriate amount of organic solvent (DMSO and ethylene glycol as a mixture of equal volume), the compound on 100mmol formula (I), 150mmol compound of formula (II), 10mmol catalyst (as 8mmol (A-taPhos)₂PdCl₂And a mixture of 2mmol trimethylphosphine (hexafluoroacetylacetonato) copper), silver trifluoroacetate 200mmol oxidant, 175 mmol alkali 16mmol DABCO accelerator and 1-butyl-3-methylimidazolium trifluoromethane sulfonimide salts, then replaced with nitrogen several times, until the reaction atmosphere is a nitrogen atmosphere; temperature was elevated to 90 deg.] C, and stirred at this temperature for 2 hours; After completion of the reaction, the reaction solution was allowed to cool to room temperature, filtered, adjusted to neutral pH of the filtrate, water was sufficiently washed with saturated brine, and then ethyl acetate was added and extracted 3 times, the organic phases combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, the resulting residue was purified by column chromatography over silica gel 300-400 mesh, in a volume ratio of 1: 2 mixture of methylene chloride and acetone, elution was carried out to afford the compound of formula (III), in a yield of 96.3%.

References:

Yang, Xiujuan CN105461528, 2016, A Location in patent:Paragraph 0045-0047

87-41-2 Synthesis