2,2-dibromo-5-methoxy-1,3-indandione

Main page (Russian)

Search in database (English)

Properties of substance:

2,2-dibromo-5-methoxy-1,3-indandione

skc-file

Synonyms:

2,2-dibromo-5-methoxy-1H-indene-1,3(2H)-dione

Group of substances:

organic

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

C₁₀H₆Br₂O₃

Synthesis 1:

Reference: Heffner, R. J., & Joullie, M. M. Synthetic Routes to Ninhydrins. Preparation of Ninhydrin, 5-Methoxyninhydrin, and 5-(Methylthio)Ninhydrin / Synthetic Communications. - 1991. - Vol. 21, No. 21 pp. 2246 [doi: 10.1080/00397919108055457]

To a solution of 5-methoxy-1,3-indanedione (0.50 g, 2.8 mmol) in dioxane (15 mL) at 15 °C, was added pyridine (0.69 mL, 8.5 mmol), followed by bromine (0.32 mL, 6.2 mmol). This mixture was allowed to warm to 25 °C. After two hours the reaction was diluted with water (35 mL), and a yellow solid precipitated. This product was removed by filtration and dried under reduced pressure, to provide 2,2-dibromo-5-methoxy-1,3-indanedione (0.90 g, 95% yield). Recrystallization from methanol and water afforded pure product, mp 137—140 °C.

R_f0.36 petroleum ether : ethyl acetate (80 : 20).

IR (CHCl3): 3030 (weak), 2990 (weak), 2960 (weak), 2860 (weak), 1770 (medium), 1730 (strong), 1610 (strong), 1585 (strong), 1495 (medium), 1460 (weak), 1440 (weak), 1360 (weak), 1350 (weak), 1290 (strong), 1265 (strong), 1170 (weak), 1100 (medium), 1080 (medium), 1020 (medium), 990 (weak), 905 (weak), 890 (weak), 870 (medium) 850 (medium) 640 (medium) cm^-1.

1H NMR (CDCl3): δ 4.05 (3H, s), 7.4 (1H, d, J = 2.3 Hz), 7.45 (1H, dd, J₁ = 2.3 Hz, J₂ = 8.1 Hz), 8.00 (1H, d, J = 8.1 Hz).

References:

Your requests if no data into database