2-Thiophenecarboxylic acid, 2-chloro-2,3-dihydro-3-oxo-, Methyl ester synthesis

Yield:95201-94-8 100%

Reaction Conditions:

with sulfuryl dichloride at 20; for 0.75 h;Irradiation;regioselective reaction;

Steps:

Experimental conditions B for the chlorination of methyl3-hydroxyheterocycles-2-yl-carboxylates (8 as an example)

General procedure: SO2Cl2 (5 M in CH2Cl2, 1.42 mL, 7.09 mmol) was added to a solution of 2 (1 g, 6.44 mmol) in CH2Cl2 (5 mL), and the mixture was stirred during 1 hour at room temperature.The mixture was concentrated in vacuo and the dry residue was purifiedby column chromatography on silica gel (EtOAc - heptane, gradient 1:0 to 7:3,v/v) to afford 8 as a yellowish solid (640 mg, 52% yield).

References:

Castillo-Aguilera, Omar;Depreux, Patrick;Halby, Ludovic;Azaroual, Nathalie;Arimondo, Paola B.;Goossens, Laurence [Tetrahedron Letters,2017,vol. 58,# 26,p. 2537 - 2541]