JPH11140003A - Production of 3, 5-bis(trifluoromethyl)iodobenzene - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound useful as an intermediate for a polymerization catalyst, an agrochemical or the like in a high yield, by reacting 1,3-bis(trifluoromethyl)benzene with iodine monochloride. SOLUTION: (A) 1,3-Bis(trifluoromethyl)benzene is reacted with (B) iodine monochloride preferably under normal pressure at 20-130 deg.C to give the objective compound. In the reaction, the amount of the component A is preferably >=1 mol based on the component B. The reaction may be carried out in the presence of a solvent inert to iodine monochloride such as acetic acid, propionic acid, dichloromethane or the like as a reaction solvent. In order to shorten the reaction time, a Lewis acid such as zinc dioxide, titanium tetrachloride, tin dichloride or the like is preferably used.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a 3,5- (3- (3- (3-phenyl) -5,5- (5,5-methyl) phenyl) ylamide useful as an intermediate for phase transfer catalysts, polymerization catalysts, pesticides, pharmaceuticals and the like.
The present invention relates to a method for producing bis (trifluoromethyl) iodobenzene.

[0002]

2. Description of the Related Art Conventionally, as a method for producing 3,5-bis (trifluoromethyl) iodobenzene, 1,3-bis (trifluoromethyl) benzene is subjected to mixed acid nitration and reduction to obtain 3,5-bis (trifluoromethyl) iodobenzene. There are known methods of converting the compound into trifluoromethyl) aniline and then diazotizing it and reacting with potassium iodide or hydroiodic acid, and a method of reacting 1,3-bis (trifluoromethyl) benzene with iodine in fuming sulfuric acid. Have been. However, the former has an extremely large number of steps, is complicated in work, and has a danger of explosion, so that industrialization is difficult. Further, the latter requires a large amount of acid waste treatment and the yield is as low as 65% or less, so that its improvement has been strongly desired.

[0003]

SUMMARY OF THE INVENTION The present invention is to provide a novel method for producing 3,5-bis (trifluoromethyl) iodobenzene which is simple, safe, high-yield and free from problems such as acid waste. It is assumed that.

[0004]

Means for Solving the Problems As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that 3,5-bis is simple, safe, has a high yield and has no problems such as acid waste. A new method for producing (trifluoromethyl) iodobenzene has been found. That is, the present invention relates to a method for producing 3,5-bis (trifluoromethyl) iodobenzene, which comprises reacting 1,3-bis (trifluoromethyl) benzene with iodine monochloride.

[0005]

DETAILED DESCRIPTION OF THE INVENTION The method of the present invention is a simple, safe, and highly efficient method for reacting 1,3-bis (trifluoromethyl) benzene with iodine monochloride to obtain 3,5-bis (trifluoromethyl) iodobenzene. It is a novel production method which has no problems such as yield and acid waste. In the present invention, the amount of iodine monochloride used may be at least 1 mol of 1,3-bis (trifluoromethyl) benzene, and is preferably 1.0 to 1. It is 2 times mol.

[0006] The reaction of the present invention may be carried out in the presence of a solvent. As a reaction solvent, acetic acid, propionic acid, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,1, inactive against iodine monochloride.
2,2-tetrachloroethane, dioxane and the like can be used. Acetic acid or propionic acid is particularly preferred for efficient reaction in a homogeneous system.

The reaction temperature may be 20 ° C. or higher, and is 20 ° C. to 130 ° C. under normal pressure, preferably 60 ° C. to 9 ° C.
0 ° C. Below 20 ° C., the reaction rate is extremely slow. At 130 ° C. or higher, iodine monochloride evaporates, so it is necessary to react under pressure. If it is necessary to shorten the reaction time, a Lewis acid catalyst such as zinc dichloride, titanium tetrachloride, tin dichloride, aluminum trichloride, boron trifluoride and the like may be added.

[0008]

EXAMPLES The present invention will be described below in detail with reference to examples, but the present invention is not limited to these examples. Example 1 1,3-bis (trifluoromethyl) benzene 214
323 g of a 50% iodine monochloride / hydrochloric acid aqueous solution was added to 300 g of acetic acid, and reacted at 75 ° C. to 85 ° C. for 11 hours. After the reaction, the mixture was cooled to room temperature, and 50 g of a 10% aqueous sodium thiosulfate solution was added. Thereafter, 300 g of toluene and 330 g of water were added, and the mixture was allowed to stand, and separated into an oil layer and an aqueous layer. The oil layer was removed, washed with 200 g of water, and then distilled under reduced pressure of 20 mmHg to a boiling point of 74 ° C to 75 ° C.
329 g of 3,5-bis (trifluoromethyl) iodobenzene was obtained as a distillate of ° C (yield: 96.8).
%).

Example 2 The same reaction and after-treatment as in Example 1 were carried out except that propionic acid was used instead of acetic acid. The yield of 3,5-bis (trifluoromethyl) iodobenzene was 97.
At 0%, good results were obtained.

Example 3 In Example 1, 1 g of zinc dichloride was further used as a catalyst.
Was added, and the mixture was reacted for 5 hours. 3,5-
The yield of bis (trifluoromethyl) iodobenzene is 9
Good results were obtained at 6.5%.

Example 4 In Example 2, the reaction was carried out at 150 ° C. for 2 hours under a nitrogen atmosphere in an autoclave at 3 to 3.5 atm.
Treated similarly. 3,5-bis (trifluoromethyl)
The yield of iodobenzene was 97.8%, and good results were obtained.

Comparative Example The method of Example 1 described in JP-A-9-227421, that is, the reaction of 1,3-bis (trifluoromethyl) benzene with iodine in fuming sulfuric acid was repeated. −
The yield of bis (trifluoromethyl) iodobenzene is 6
It was as low as 1.5%. In addition, a large amount of sodium hydroxide solution is required for waste sulfuric acid treatment, and the operation is difficult due to heat generation.

[0013]

Industrial Applicability The present invention provides a simple, safe, high-yield, and acid-soluble 3,5-bis (trifluoromethyl) iodobenzene useful as an intermediate for phase transfer catalysts, polymerization catalysts, agricultural chemicals, pharmaceuticals and the like. It has made it possible to provide a production method free from problems such as waste.

Claims (2)

[Claims] 1. A method for producing 3,5-bis (trifluoromethyl) iodobenzene, comprising reacting 1,3-bis (trifluoromethyl) benzene with iodine monochloride. 2. The method for producing 3,5-bis (trifluoromethyl) iodobenzene according to claim 1, wherein the reaction solvent is acetic acid.