Synonyms:

Group of substances:

Empirical formula (Hill's system for organic substances):

Synthesis 1:

To a solution of 6-(methylthio)-1-indanone (1.00 g, 5.16 mmol) in carbon tetrachloride (40 mL) at 25 °C, was added dry recrystallized N-bromosuccinimide (2.99 g, 16.8 mmol) and azobisisobutyronitrile (29.3 mg, 0.18 mmol). The mixture was heated at reflux, while being illuminated with a 125W light. After five hours the reaction was cooled to 5 °C, and triethylamine (2.74 mL, 19.6 mmol) was added and the reaction mixture was allowed to stir for one hour at 25 °C. Solids were collected by filtration, and washed with carbon tetrachloride. The filtrate was washed with 1 N HCl solution (20 mL), 5% NaHCO3 solution, then water. The organic layer was dried over Na2SO4, filtered, then concentrated under reduced pressure to afford a solid. This material was purified by column chromatography using petroleum ether : methylene chloride (50 : 50), to provide solid 2,3-dibromo-6-(methylthio)-1-indenone (0.91 g, 50% yield, R_f 0.63), solid 3-bromo-6-(methylthio)-1-indenone (0.23 g, 16% yield, R_f 0.54), and 6-(methylthio)-1-indenone as an oil (0.085 g, 9% yield, R_f 0.34). The solid was recrystallized from hexane to provide pure compound, mp 80—82 °C.

HRMS calcd. for C10H7BrOS (M+): 253.940. Found: 253.943.

IR (CHCl3): 3005 (weak), 2940 (weak), 1750 (weak), 1710 (strong), 1600 (medium), 1530 (weak), 1465 (weak), 1440 (medium), 1415 (medium), 1350 (weak), 1320 (weak), 1290 (weak), 1260 (medium), 1180 (medium), 1180 (weak), 1040 (weak), 970 (weak), 950 (weak), 860 (weak), 825 (strong) cm^-1.

1H NMR (CDCl3): δ 2.52 (3H, s), 6.15 (1H, s), 7.17 (1H, d, J = 7.6 Hz), 7.26 (1 H, dd, J₁ = 1.7 Hz, J₂ = 7.6 Hz), 7.29 (1H, d, J = 1.7 Hz).

References:

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© Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru