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A technology of dibromohydantoin and dibromohydantoin, which is applied in the preparation of organic compounds, carbon-based compounds, heterocyclic compounds, etc., can solve the problems of low yield and inconvenient operation, and achieve easy-to-obtain raw materials and easy operation , low-cost effect
Active Publication Date: 2018-04-03
FUDAN UNIV
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The prior art discloses that the traditional preparation method of this type of compound is to use ketone as a raw material, and use bromine or other bromine sources to carry out bromination ((1) J.Am.Chem.Soc.1913,35,1770-1774; (2 )TetrahedronLett.1984,25,3369-3372; (3)Synth.Commum.2002,32,3711-3717); This method requires the use of toxic reagents, low yield and inconvenient operation
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Embodiment 1
[0022] Example 1 Preparation of 2,2-dibromoacetophenone
[0023] Using styrene as raw material, prepared according to the general method, the yield is 87%, and the NMR spectrum data of the product are as follows: 1 HNMR (400MHz, CDCl 3 )δ8.10–8.05 (m, 2H), 7.64 (t, J = 7.4Hz, 1H), 7.51 (t, J = 7.7Hz, 2H), 6.72 (s, 1H).
Embodiment 2
[0024] Example 2 Preparation of 2,2-dibromo-2'-methylacetophenone
[0025] Using o-methyl styrene as raw material, it is prepared according to the general method, and the yield is 70%. The NMR spectrum data of the product are as follows: 1 HNMR (400MHz, CDCl 3 ) δ 7.68 (d, J = 7.6Hz, 1H), 7.46 (t, J = 7.3Hz, 1H), 7.34–7.28 (m, 2H), 6.68 (s, 1H), 2.52 (s, 3H).
Embodiment 3
[0026] Example 3 Preparation of 2,2-dibromo-4'-methylacetophenone
[0027] Taking p-methylstyrene as raw material, it is prepared according to the general method, and the yield is 80%. The NMR spectrum data of the product are as follows: 1 HNMR (400MHz, CDCl 3 ) δ 7.98 (d, J = 8.3Hz, 2H), 7.31 (d, J = 8.0Hz, 2H), 6.70 (s, 1H), 2.44 (s, 3H).
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Abstract
The invention belongs to the field of preparation of fine chemical products and synthesis of pharmaceutical intermediates and relates to a preparation method of novel alpha, alpha-dibromoketone, in particular to a method for converting olefin into alpha, alpha-dibromoketone by use of dibromohydantoin or N-bromosuccinimide. Compared with the reported methods, the method has the advantages that rawmaterials are easy to obtain and low in cost, used reagents have smaller toxicity, and the method has greater cost and environmental protection advantages and wide application prospects.
Description
technical field [0001] The invention belongs to the fields of preparation of fine chemical products and synthesis of pharmaceutical intermediates, and specifically relates to a new method for converting olefins into alpha, alpha-dibromoketones by using dibromohydantoin or N-bromosuccinimide. Background technique [0002] alpha, alpha-dibromoketones are widely used in organic chemistry, medicinal chemistry, biochemistry and material science. The prior art discloses that the traditional preparation method of this type of compound is to use ketone as a raw material, and use bromine or other bromine sources to carry out bromination ((1) J.Am.Chem.Soc.1913,35,1770-1774; (2 ) Tetrahedron Lett.1984, 25, 3369-3372; (3) Synth. Commum. 2002, 32, 3711-3717); This method requires the use of more toxic reagents, low yield and inconvenient operation. In recent years, researchers have turned to alkynes as raw materials for the preparation of alpha, alpha-dibromoketones (J.Org.Chem.1994,59...
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