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Synthesis of 3-Bromo Flavones from 2-Hydroxy-3, 5-Dibromo-4’nitro Dibenzoyl Methane

Volume 28, Number 3

R.E. Bhadange1 and R. P. Ganorkar2

1Department of Chemistry, ShriShivaji College, Akola - 444 101, India. 2Department of Chemistry, Mahatma FuleArts,Commerce and Sitaramji Chaudhari Science Mahavidyalaya, Warud Dist. Amravati - 444 906 India.

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ABSTRACT:

A new 3-bromo substituted flavones have been synthesized by the reaction of 2- hydroxy-3, 5-dibromo-4'nitro dibenzoyl methane was dissolved in dimethyl formamide (DMF) and pure bromine was added. The mixture was refluxed for 1-3 hours. Then cooled, diluted with ice-cold water and crystallized from alcohol-acetic acid mixture to get 2(4'nitrophenyl)-3,6, 8-tribromo flavones.The structures of all newly synthesized compounds were confirmed on the basis of IR,NMR. The melting points were taken in an open capillary tube.

KEYWORDS:

Synthesis; Dibenzoyl methane; Bromo-Flavones

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Bhadange R. E, Ganorkar R. P. Synthesis of 3-Bromo Flavones from 2-Hydroxy-3, 5-Dibromo-4’nitro Dibenzoyl Methane. Orient J Chem 2012;28(3).

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Bhadange R. E, Ganorkar R. P. Synthesis of 3-Bromo Flavones from 2-Hydroxy-3, 5-Dibromo-4’nitro Dibenzoyl Methane. Available from: http://www.orientjchem.org/?p=23175

Introduction:-

Flavones constitute large segment of natural products.Synthesis of flavones has attracted considerable attention due to their significant biocidal1-3, pharmaceutical 4-7anti- cancer8 and anti-inflammatory 9-10effects.Dibenzoyl methane reacts in DMF medium or with bromine in DMF to give 3-halo flavones11. 1, 3 diketones was transformed into 7-hydroxy-6-nitro flavone12.Some new biologically active chalcones and flavones have been synthesized 13.3-chloro flavones were prepared by action of thionyl chloride or sulphuryl chloride with flavones14-16. Antibacterial activity of some new chalconesand flavones having 2-chloro-8-methoxyquinolinyl moiety17.

The literature  survey clearly indicates that 3-bromo substituted flavones are not  yet synthesized. It was therefore thought of interest to synthesis 2(4’nitrophenyl)-3, 6, 8-tribromo flavones from 2- hydroxy-3, 5-dibromo-4‘nitro dibenzoylmethane(IIa).  2- hydroxy-3, 5-dibromo-4‘nitro dibenzoyl methane (0.01 moles) (Ia) was dissolved in dimethyl formamide (DMF) and pure Bromine (0.01 moles) was added. The mixture was refluxed for 1-3 hours. Then cooled, diluted with ice-cold water and crystallized from alcohol-acetic acid mixture to get 2(4’nitrophenyl)-3, 6, 8-tribromo flavones (IIa). Structures of  these compounds  have been established by spectral analysis.

 EXPERIMENTAL:-

Melting point were taken in  Silicon Oil bath instrument in open capillary and are uncorrected . Purity of the compounds was checked by TLC on silica gel G plates. IR spectra were recorded in Nujol, H1 NMR spectra were recorded in CDCl3 with TMS as an internal standard.

 Preparation of 2-(4′-nitrophenyl)-3,6-8-tribromo flavones (IIa):-

2- hydroxy-3, 5-dibromo-4‘nitro dibenzoyl methane (0.01 moles) was dissolved in dimethyl formamide (DMF) and pure Bromine (0.01 moles) was added. The mixture was refluxed for 1-3 hours. Then cooled, diluted with ice-cold water and crystallized from alcohol-acetic acid mixture to get 2(4’nitrophenyl)-3, 6, 8-tribromo flavones (IIa), m.p.-1690c.

It show negative ferric chloride solution test indicate the involvement of phenolic –OH group in cyclization.

Similarly other compounds (II a-i) were prepared by above method.

scheme 1

Scheme of Compounds  (IIa-i)

Spectral interpretation of (2i)

IR spectrum was recorded in Nujol.

IR(υmax)cm-1 :-

  • 1663 cm-1(C=0).
  • 1590cm-1 (C=C).
  • 1249 cm-1                           (C-O-C )
  • 702 cm-1                          (-C-Br).

 NMR :-

H PMR was recorded in CDCl3 with TMS as internal standard.

  • 6.85-7.97 δ    (m, 6H, Ar-H).

 

Physical  data of synthesized  2-(4′-nitrophenyl)-3,6-8-tribromo

flavones (IIa)

Sr.No.

compounds

R1

R2

M.P(0C)

Yields in %

1

IIa

Br

NO2

111

60

2

IIb

Br

Cl

178

76

3

IIc

Br

NH2

138

69

4

IId

NO2

NO2

252

75

5

IIe

NO2

Cl

206

73

6

IIf

NO2

NH2

131

80

7

IIg

H

NO2

293

78

8

IIh

H

Cl

224

72

9

IIi

H

NH2

261

71

AKNOWLEDGEMENT:

The authors are thankful to Department of Chemistry ShriShivaji College Akola & Mahatma Fule Arts, Commerce And SitaramjiChaudhari Science Mahavidyalya, Warud  for their valuable Support and necessary laboratory facilities during research work.

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