Dibenzothiophene → 2-Methyl-1,2-dihydrobenzo[b]indeno[4,5-d]thiophen-3-one

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Reaction Steps

20 g (108.7 mmol) of dibenzothiophene (1) were added at −78° C. to an agitated solution of 10.6 ml methacryloyl chloride (108.7 mmol) and 15.3 g AlCl3 (114.8 mmol) in 250 ml methylene chloride and brought to room temperature overnight. The solution was hydrolysed carefully at 0° C., the organic phase was separated, washed with an aqueous solution of K2CO3 and dried over Na2SO4. After removal of the solvent and crystallisation in toluene/pentane≈10:1, 2-methyl-1,2-dihydrobenzo[b]indeno[4,5-d]thiophen-3-one (2) was obtained as crystalline solid material (21.6 g, 85.9 mmol, 79%).

Provenance & Evidence