1-tosyl-3-acetylpyrrole → 2-Chloro-1-[1-(4-methylbenzene-1-sulfonyl)-1H-pyrrol-3-yl]ethan-1-one

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Reaction Steps

In a 100 cm3 one neck flask fitted with a condenser and a calcium chloride guard, 4 g of 3-acetyl-1-tosyl pyrrole 2 (15 mmoles) was introduced together with 30 cm3 of methanol. Then 4.5 g of 2,3,4,5,6,6-hexachloro-2,4-hexadiene-1-one (15 mmoles) was set under reflux during 6 hours and maintained under stirring at ambient temperature during one night. The solvent was evaporated and the crude product (8.5 g) was dissolved in 15 cm3 of chloroform, filtered (the pentachlorophenol was not very soluble in this solvent) and separated on silica gel column (250 g; 60-200 82 m; eluting with 1-29-70 acetic acid-ethyl acetate-heptane; VR =650 cm3) to give 2.35 g of white crystals 3 (M=297.5, yield: 53%).

Provenance & Evidence