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1,3-bis(2-bromo-5-methoxylstyryl)-2,4,6-trinitrobenzene and preparation method thereof

A technology of methoxystyrene and trinitrobenzene, applied in 1, can solve the problems of limited compounds, side-chain side reactions, poor regioselectivity, etc., and achieve the effect of good symmetry

Active Publication Date: 2015-11-11
安徽伟祥新材料有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these methods have been widely used, they still have several significant disadvantages: 1. The applicable compounds are relatively limited; 2. There are side chain side reactions and excessive bromination; 3. Single bromination results; 4. Regional Poor selectivity, resulting in waste of raw materials and a large amount of waste liquid

Method used

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  • 1,3-bis(2-bromo-5-methoxylstyryl)-2,4,6-trinitrobenzene and preparation method thereof
  • 1,3-bis(2-bromo-5-methoxylstyryl)-2,4,6-trinitrobenzene and preparation method thereof
  • 1,3-bis(2-bromo-5-methoxylstyryl)-2,4,6-trinitrobenzene and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: 1,3-bis(3-methoxystyryl)-2,4,6-trinitrobenzene (0.48g), liquid bromine (0.32g), H-Beta molecular sieve (0.05g), zinc oxide (0.05g) and dichloromethane (10mL) were added to the reactor, reacted at room temperature for 24h, filtered, extracted, and rotary evaporated to obtain 0.61g of an orange-yellow crude product, which was recrystallized with acetone and ethanol to obtain an orange-yellow pure product 0.59g, melting point 211.2-213.2°C, yield 96.7%.

[0018] IR(KBr,ν,cm -1 ):3095,1634,1590,1539,1332,970; 1 HNMR (300MHz, CDCl 3 ),δ8.85(s,1H),7.52(d, J =8.7Hz,2H),7.18-7.15(m,6H),6.86-6.82(m,2H),3.88(s,6H); 13 CNMR (75MHz, DMSO-d 6 ), δ159.36, 147.12, 135.50, 134.68, 134.26, 130.58, 123.35, 121.66, 117.85, 114.57, 112.95, 56.04.

Embodiment 2

[0019] Example 2: 1,3-bis(3-methoxystyryl)-2,4,6-trinitrobenzene (0.48g), liquid bromine (0.32g), H-Beta molecular sieve (0.1g), zinc oxide (0.05g) and dichloromethane (10mL) were added to the reactor, reacted at room temperature for 24h, filtered, extracted, and rotary evaporated to obtain 0.61g of an orange-yellow crude product, which was recrystallized with acetone and ethanol to obtain an orange-yellow pure product 0.55g, the yield is 90.2%.

Embodiment 3

[0020] Example 3: 1,3-bis(3-methoxystyryl)-2,4,6-trinitrobenzene (0.48g), liquid bromine (0.32g), H-Beta molecular sieve (0.02g), zinc oxide (0.05g) and dichloromethane (10mL) were added to the reactor, reacted at room temperature for 24h, filtered, extracted, and rotary evaporated to obtain 0.53g of an orange-yellow crude product, which was recrystallized with acetone and ethanol to obtain an orange-yellow pure product 0.42g, yield 79.2%.

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Abstract

The invention discloses 1,3-bis(2-bromo-5-methoxylstyryl)-2,4,6-trinitrobenzene and a preparation method thereof. The preparation method comprises the following steps: adding 1,3-bis(3-methoxylstyryl)-2,4,6-trinitrobenzene, liquid bromine, and a catalyst into a reactor, taking dichloromethane as the solvent, carrying out reactions at the room temperature, after reactions, filtering, neutralizing the filtrate by a saturated sodium carbonate solution, extracting the filtrate by dichloromethane, carrying out spinning evaporation, and finally drying to obtain 1,3-bis(2-bromo-5-methoxylstyryl)-2,4,6-trinitrobenzene. Each benzene ring on the periphery of 1,3-bis(2-bromo-5-methoxylstyryl)-2,4,6-trinitrobenzene contains a bromine atom, the symmetrical property is good, moreover, the central benzene ring is connected to two other benzene rings through two conjugated double bonds, and thus the stability of the compound is greatly improved. The provided compound can be used to produce functional materials used in the fields such as medicine, pesticide, heatproof materials, and the like.

Description

technical field [0001] The invention relates to a 1,3-bis(2-bromo-5-methoxystyryl)-2,4,6-trinitrobenzene compound and a preparation method thereof, belonging to flame retardants, insecticides and medicines intermediate. Background technique [0002] The conjugation effect between the double bond and the benzene ring in the structure of the stilbene compound makes the chemical property of the compound relatively stable. If multiple nitro groups are introduced on the benzene ring, it will be more stable, and the bromination conditions will become more severe. So far, many bromination methods have been developed, such as NBS?H 2 SO 4 ?TFA, DBUHBr 3 、Br 2 ?Lewisacids, KBr / BTPPMS, ZrBr 4 / diaziene, IQBC, and [BMPy]Br 3 etc. Although these methods have been widely used, they still have several significant disadvantages: 1. The applicable compounds are relatively limited; 2. There are side chain side reactions and excessive bromination; 3. The results of bromination are sin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/35C07C201/12
Inventor 唐鹏飞郝征彭新华沈坚
Owner 安徽伟祥新材料有限公司
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