2,2,2-TRICHLORO-1-(4,5-DICHLORO-1H-PYRROL-2-YL)ETHANONE synthesis

Yield:50371-51-2 85%

Reaction Conditions:

with thionyl chloride in dichloromethane at 20; for 108 h;Inert atmosphere;Darkness;

Steps:

2,2,2-Trichloro-1-(4-chloro-1H-pyrrol-2-yl)ethan-1-one 2b

General procedure: To a stirring solution of pyrrole 2a (3.4 g, 16.2 mmol) in CH2Cl2 (80 mL) in 0 °C was addedsulfuryl chloride (1.57 mL, 19.4 mmol) in CH2Cl2 (10 mL) dropwise. The reaction wasprotected by light and stirred at r.t. for 18 h. The reaction mixture was then diluted with CH2Cl2(20 mL), poured onto ice, and quenched with sat. aq. sodium bicarbonate (10 mL). The reactionmixture was extracted with CH2Cl2 (3 x 20 mL) and the combined organic extracts washedwith brine (50 mL) and dried (MgSO4). The solvent was removed in vacuo to give the crudeproduct, which was purified by flash chromatography (8:92 Et2O:petroleum ether) to afford thetitle compound 2b (2.5 g, 63%) as a pale cream solid. Rf = 0.17 (8:92 Et2O:petroleum ether).m.p. 119-121 °C. (lit. m.p. 119-121 °C).

References:

Barker, David;Lee, Stephanie;Varnava, Kyriakos G.;Sparrow, Kevin;van Rensburg, Michelle;Deed, Rebecca C.;Cadelis, Melissa M.;Li, Steven A.;Copp, Brent R.;Sarojini, Vijayalekshmi;Pilkington, Lisa I. [Molecules,2020,vol. 25,# 11,art. no. 2713] Location in patent:supporting information