5-bromoacenaphthylene-1,2-dione synthesis
- Product Name:5-bromoacenaphthylene-1,2-dione
- CAS Number:26254-35-3
- Molecular formula:C12H5BrO2
- Molecular Weight:261.07
2051-98-1
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Yield:26254-35-3 76%
Reaction Conditions:
with sodium dichromate dihydrate;cerium(III) chloride heptahydrate in acetic acid at 40; for 8 h;
Steps:
Synthesis of 5-bromacenaphthenequinone. Sodiumbichromate dihydrate (23.9 g, 80.2 mmol) was addedby small portions with continuous stirring to a solutionof 5-bromacenaphthene (11.0 g, 47.2 mmol) andcesium chloride heptahydrate (0.5 g, 1.3 mmol) inacetic acid (50 mL) at 40° for 1 h. The reaction mixturewas stirred at 40° for 8 h, and cold water (1 L) was added. The precipitate formed was filtered off onthe Büchner funnel and washed with water. Theformed solid substance with a 10% solution of soda(200 mL) was stirred at 80° for 30 min, separated byfiltration on the Büchner funnel, and washed withwater. The precipitate was extracted with a 4% aqueoussolution of sodium bisulfate (500 mL) at 80° for30 min. The obtained filtrate was acidified with concentratedsulfuric acid with permanent stirring toreach a weakly acidic pH of the solution. The precipitatedyellow substance was filtered off, consecutivelywashed with water and ethanol, and dried in vacuo.The yield was 9.4 g (76%), mp > 238 (decomp.).1 NMR (200 MHz, DMSO-d6, 300 K; J, Hz), δ,ppm: 8.37 (d, 1, J = 8.2), 8.24-8.09 (m, 2), 8.04(d, 1, J = 7.6), 7.93 (d, 1, J = 7.2).IR (ν, cm-1): 2362 w, 1730 s, 1684 w, 1604 w,1576 w, 1507 w, 1304 w, 1268 w, 1209 w, 1117 w,1083 w, 1020 m, 943 w, 897 w, 847 w, 818 w, 794 w,768 m, 724 w.
References:
Baranov, E. V.;Dodonov, V. A.;Fedushkin, I. L.;Koptseva, T. S.;Makarov, V. M.;Skatova, A. A.;Sokolov, V. G. [Russian Journal of Coordination Chemistry,2020,vol. 46,# 4,p. 215 - 223][Koord. Khim.,2020,vol. 46,# 4,p. 195 - 203,9]
82-86-0
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83-32-9
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