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ChemicalBook CAS DataBase List 3-Acetyl-2,5-dichlorothiophene
36157-40-1

3-Acetyl-2,5-dichlorothiophene synthesis

2synthesis methods
1-Methyl-4-chlorobutenal was reacted with a strong base to remove the active hydrogen at the α-position, then docked with thioacetyl chloride and reacted at 60-80 degrees Celsius to obtain the target product 3-acetyl-2,5-dichlorothiophene.
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Yield:36157-40-1 90%

Reaction Conditions:

with aluminum (III) chloride in carbon disulfide at 20; for 25 h;Friedel-Crafts Acylation;

Steps:

Synthesis of Starting Materials
Scheme 1 outlines the synthesis of all starting materialsand the title compound. The synthesis of 3-acetyl-2,5-dichloro-thiophene, 2, was accomplished as described in literature [9]. A solution of 2,5-dichlorothiophene, 1,(15.2 g, 100 mmol) in dry carbon disulfide (25 ml) was added dropwise, during 1 h, to a stirred mixture of anhydrous AlCl3 (15.0 g, 110 mmol) and acetyl chloride (7.9 g,100 mmol) in dry CS2 (80 ml). The reaction mixture was stirred at RT for 24 h. Cold water (50 ml) was then added dropwise to the reaction with continuous stirring for 30 min the organic layer was separated, washed with water (4 x 30 ml), dried over anhydrous CaCl2 and the solvent was evaporated to produce a solid product. Yield: 80 % [9].

References:

Al-Refai, Mahmoud;Ibrahim, Mohammad M.;Geyer, Armin;Marsch, Michael;Ali, Basem F. [Journal of Chemical Crystallography,2016,vol. 46,# 8-9,p. 331 - 340]

FullText

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