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Method for preparing and recovering aromatic methyl diphenyl compound

A technology for aromatic methyl biphenyl and aromatic bromomethyl biphenyl, which is applied in the field of industrial preparation and recovery of aromatic methyl biphenyl compounds, can solve problems such as high price and limitation, and achieve the effect of improving utilization rate

Active Publication Date: 2010-07-07
ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the above method uses expensive catalysts such as palladium and nickel, and also uses hydrogen, which requires higher requirements for operation.
This limits the application of this method

Method used

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  • Method for preparing and recovering aromatic methyl diphenyl compound
  • Method for preparing and recovering aromatic methyl diphenyl compound
  • Method for preparing and recovering aromatic methyl diphenyl compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0034] Add 50g (0.2588mol) of 4'-methyl-2-cyanobiphenyl (OTBN) and 300ml of dichloromethane into a four-neck flask, set the internal temperature at 35-40°C, add light, and add it dropwise within 3 hours 22.8g (0.1425mol) bromine, 30g (content 27.5%, 0.2426mol) hydrogen peroxide, and then keep warm at 35-40°C for 3 hours, take a sample, and analyze by HPLC. The mixture was found to contain 5.1% 4'-methyl-2-cyanobiphenyl, 85.5% 4'-bromomethyl-2-cyanobiphenyl, 9.2% 4'-dibromomethyl-2-cyanobiphenyl benzene.

[0035] Then, the water layer was separated, and the organic phase was distilled out of dichloromethane, and 250ml of toluene was added for separation and purification to obtain 4'-bromomethyl-2-cyanobiphenyl with a purity of 53.8g (HPLC) of 97.8%. The yield was 76.4%. % (based on 4'-methyl-2-cyanobiphenyl). Then, the toluene in the mother liquor after separation of the product was distilled off to obtain 12.2 g of the mixture. HPLC analysis found that the mixture contained...

Embodiment 1

[0037] Add 5g (0.0769mol) of zinc powder, 6g (0.1121mol) of ammonium chloride, and 100ml of toluene into a three-necked flask, set the internal temperature at 45-50°C, and stir; in addition, dissolve the mother liquor mixture obtained in the above preparation example in 60ml of toluene , and then drop it into a three-necked flask for about 1 hour, then keep warm at 45-50°C for 18 hours, filter, wash, remove impurities such as inorganic salts, distill toluene, and then fractionally distill to obtain 6.7g of 4'-methyl-2- Cyanobiphenyl, GC analysis purity 97.5%.

Embodiment 2

[0039] According to the method of Preparation Example 1, 14.1g of the mixture was obtained. According to HPLC analysis, the mixture contained 30.1% 4'-methyl-2-cyanobiphenyl, 29.7% 4'-bromomethyl-2-cyanobiphenyl, 39.7% % 4'-Dibromomethyl-2-cyanobiphenyl.

[0040]Add 8g (0.1231mol) of zinc powder, 12g (0.0909mol) of ammonium sulfate, and 200ml of toluene into a three-necked flask, set the internal temperature at 70-75°C, and stir; in addition, dissolve the above mother liquor mixture in 80ml of toluene, and then dissolve it for about 1 hour. Add it dropwise to a three-necked flask, keep warm at 70-75°C for 12 hours, filter, wash, remove impurities such as inorganic salts, distill toluene, and then fractionally distill to obtain 8.1g of 4'-methyl-2-cyanobiphenyl, GC analysis purity 98.0%.

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Abstract

The invention provides a method for preparing and recovering aromatic methyl diphenyl compound (I), wherein, an aromatic methyl diphenyl compound (I) is used for preparing an aromatic bromomethyl diphenyl compound (II), after separating and purifying the product, the aromatic halomethyl diphenyl compound (II) and a compound (III) are contained in a mother liquor, that is: the aromatic methyl diphenyl compound in the mother liquor is reacted with proton donor and active metallic zinc in the solvent and then converted into the aromatic methyl diphenyl compound. By adopting the method, the aromatic halomethyl diphenyl compound in the mother liquor can be converted into the aromatic methyl diphenyl compound for recycle, which has obvious utility value in industrial applications. The aromatic methyl diphenyl compound (I), the aromatic bromomethyl diphenyl compound (II) and the aromatic bibromomethyl diphenyl compound (II) are provided.

Description

technical field [0001] The invention relates to a method for industrially preparing and recovering aromatic methyl biphenyl compound (I). The aromatic methyl biphenyl compound (I) is a raw material for synthesizing the aromatic bromomethyl biphenyl compound (II), and the aromatic bromomethyl biphenyl compound (II) can be used as a synthetic intermediate of a pharmaceutical product. Background technique [0002] Arylmethyl biphenyl compound (I) is an important intermediate in the synthesis of pharmaceutical products. [0003] It is described in U.S.Pat.No.6214999 that in the presence of a free radical initiator, aromatic methyl biphenyl compound (I) reacts with NBS, dibromohydantoin (DBDMH) as a brominating agent to prepare aromatic bromomethyl biphenyl The method of benzene compound (II). [0004] WO99 / 33788 describes a method for preparing an aromatic bromomethyl biphenyl compound (II) by reacting an aromatic methyl biphenyl compound (I) with bromine as a brominating agen...

Claims

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Application Information

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IPC IPC(8): C07B35/06C07C255/50C07C253/30C07D257/04
Inventor 黄盛平涂国良金永君
Owner ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD
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