Chlorosulfonic acid → 1-Indanone, 6-bromo-

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Reaction Steps

To chlorosulfuric acid (1.19 L) was added 3-(4-bromophenyl)propanoic acid (91.1 g) under ice cooling and the mixture was stirred for 2 hours. To H2O (2.00 L), the reaction mixture was slowly added under ice cooling, and extracted 6 times with CHCl3. The combined organic layers were washed with a saturated aqueous NaHCO3 solution, dried over Na2SO4 and concentrated under reduced pressure. To the resultant residue, MeOH was added and the mixture was heated to reflux for 30 minutes. A solid substance was obtained by filtration to give solid A. The filtrate was concentrated under reduced pressure and solid B was obtained in the same manner. Thereafter, the filtrate was again concentrated under reduced pressure and solid C was obtained in the same manner. Solids A, B and C were combined to obtain 6-bromo-2,3-dihydro-1H-inden-1-one (59.3 g, a light yellow solid).

Provenance & Evidence