KR950004174B1 - 2-aryl propylsilanes and method of preparing the same - Google Patents

Abstract

The 2-aryl propyl silane of formula (III) is prepared by the friedel-crafts reaction of an aromatic compound of formula (I) and an allyl silane of formula (II) in the presence of a lewis acid catalyst i.e. aluminium chloride at 0-50 deg.C. In the formulas, R and R' are each H, C1-4 alkyl, phenoxy, F, Cl, Br, mercapto, mercapto methyl; Ar is aryl; X1, X2 and X3 are each H or Cl. The 2-aryl propyl silane is used as a starting material in the production of an organic silicon polymer compound.

Description

2-arylpropylsilanes and preparation method thereof

The present invention relates to 2-arylpropylsilanes of general formula (III) and methods for their preparation.

In more detail, the aromatic compounds of Formula (I) and allylsilanes of Formula (II) are catalyzed by a Predal-Craft reaction with Lewis acids such as aluminum chloride. A new and advanced process for the preparation of 3-arylpropylsilane is an important starting material for the preparation of organosilicon polymer compounds.

Wherein R and R 'are independently hydrogen, a C ₁ -C ₄ carboxyl group, phenoxy group, fluoro, chloro, bromo, mercapto, mercaptomethyl group and Ar is benzene ring, naphthalene ring, biphenyl An aryl group such as a ring is represented, and X ₁ , X ₂ and X ₃ each represent a hydrogen or chloro group. However, when X ₁ , X ₂ and X ₃ are all chloro groups, R is hydrogen and R 'is chloro or bromo group, except that when R and R' are hydrogen, X ₁ , X ₂ and X ₃ are Except when both are chloro groups and when X ₁ is hydrogen and X ₂ and X ₃ are chloro groups.

In 1945, Hurd first published the synthesis of allylsilanes by direct reaction of allyl chloride and silicon (D. T. Hurd, J. Am. Chem. Soc., 67, 1813 (1945)). He obtained trichlorosilane, tetrachlorosilane, allyldichlorosilane, allyltrichlorosilane, and diallyldichlorosilane in this reaction. In addition to the allyldichlorosilane, which is the expected product, various compounds are produced because allyl chloride, which is a reaction starting material, decomposes under reaction conditions. Furthermore, of the three products substituted with allyl groups, the most produced compound was trichloroallylsilane, not diallyldichlorosilane. This process is very difficult to perform because diallyldichlorosilane readily polymerizes at temperatures above 130 ° C., resulting in a nonvolatile polymer.

Myronov and his co-workers reported that 20% of the copper catalyst was added to silicon and reacted with 2Kg of allyl chloride at 300 ° C to obtain only 644g of allyl-substituted product. Among the products, allyldichlorosilane was obtained most at 356g, and then allyltrichlorosilane was obtained at 185g and diallyldichlorosilane was obtained at least 103g (VM Mironov and DN Zelinskii, Isvest. Akad. Nauk SSSR, Otdel, Khim Nauk 383 (1957). Even in this reaction, the low yield below 30% indicates that there is no economic feasibility. In addition, the production of allyldichlorosilane and allyltrichlorosilane much indicates that the starting material allyl chloride is decomposed to generate chlorine or hydrogen chloride.

The present inventors could mix allyl chloride with hydrogen chloride to react with silicon to obtain two silanes, allyldichlorosilane and trichloroallylsilane. This suggests that the reactivity of allyl chloride and hydrogen chloride is similar so that a compound in which each of these two molecules enters one silicon atom can be obtained. In this process, since there is little generation of dichlorodiallylsilane, which is easy to polymerize, there is no difficulty in performing the process (Korean Patent Application No. 92-10292 (1992.6.13.))

Petrov and his co-workers reported that allyldichlorosilanes can be obtained by disproportionation of pyridine as catalysts (AD Petrov and VM Vdovin, Izv. Akad. Nauk SSSR, Otdel Khim). Nauk 519, (1960).

Nametkin and his co-workers have reported that allylsilane can be added to aromatic compounds by a predal-craft reaction (NS Nametkin, VM Vdovin, ES Finkelshtein, VDOppengelum, and NA Chekalina, Izv. Akad. Nauk SSSR, Ser.Khim., 1966 (11), 1998-2004). They added allyltrichlorosilane, allyldichlorosilane, allylmethyldichlorosilane and allyltrimethylsilane to benzene, chlorobenzene, bromobenzene, benzyl trichlorosilane under an aluminum trichloride catalyst to give 2-phenylpropylsilane.

In the same manner, allyldichlorosilane was added to benzene to give a yield of 60%.

In the present invention, the aromatic compounds of general formula (I) and allylsilanes of general formula (II) are catalyzed by Lewis acids such as aluminum chloride to form 2-arylpropylsilane of general formula (III) by a predal-craft reaction. It was found that it could be synthesized.

Wherein R and R 'are independently hydrogen, an alkyl group of C ₁ -C ₄ , a phenoxy group, a fluoro, chloro, bromo, mercapto, mercaptomethyl group and Ar is a benzene ring, naphthalene ring, biphenyl ring Aryl groups such as X ₁ , X ₂ , and X ₃ each represent a hydrogen or chloro group. However, when X ₁ , X ₂ , and X ₃ are all chloro groups, R is hydrogen, except when R 'is chloro or bromo group, and when R and R' are hydrogen, X ₁ , X ₂ , X ₃ is Except when both are chloro groups and when X ₁ is hydrogen and X ₂ and X ₃ are chloro groups.

As a catalyst, Lewis acids such as aluminum chloride may be used, and may be mixed with chloride compounds such as zinc, boron, titanium, iron, repayment, cadmium, and antimony as necessary. The catalyst is preferably mixed with the compound of formula (I), and then allylsilane of the formula (II) is added to the mixture. On the contrary, when the catalyst is put in allylsilane of the general formula (II), the allyl group of allylsilane can be polymerized by the catalyst. Since this reaction is exothermic, the reaction heat is effectively removed to prevent the temperature of the reactor from becoming high. If the compound of the formula (I) is a liquid, it is not necessary to use a solvent, but if it is a solid, it is preferable to use a suitable solvent. The solvent is not suitable for aromatic compounds and ethers, and solvents such as hexane and carbon tetrachloride are suitable.

In the present invention, if the ratio of the compound of the general formula (I) is not large in the amount of the reactants of the general formula (I) and the general formula (II), the product to which 2 moles of the compound of the general formula (II) is added is obtained as some by-product. Lose. As in the case where a by-product is obtained, various functional groups can be introduced into the aromatic ring by reacting 1 mol of allylsilane of the general formula (II) and then reacting another reactant having a good predal-craft reaction.

The following examples will further illustrate the invention, but the invention is not limited thereto.

(Example 1)

Preparation of 3- (methylphenyl) -1,1-dichloro-1-silabutane

The 100m1 round bottom flask was equipped with a reflux condenser and a dropping funnel, followed by flame drying while passing the dried N ₂ gas. Aluminum chloride, 0.9 g (0.007 mol) and toluene, 19.3 g (0.21 mole) were placed in a round bottom flask. 10.0 g (0.07 mole) of allyldichlorosilane was added to the dropping funnel. Allyldichlorosilane was added dropwise for 30 minutes while the flask was cooled in an ice bath, followed by further stirring for 1 hour. The end of the reaction was confirmed by gas chromatography. After the reaction was completed, NaCl, 2.0g (0.03mole) was added and the reaction temperature was raised to 50 ℃ and stirred for 30 minutes to remove the activity of the catalyst. The reaction product was vacuum distilled (73-6 ° C./0.6 mmHg) to give 3- (4-methylphenyl) -1,1-dichloro-1-silabutane and 3- (2-methylphenyl) -1,1-dichloro-1- 11.7 g (71%) of a mixture of silabutane mixed with 2: 1 was obtained.

(Example 2)

Preparation of 3- (dimethylphenyl) -1,1-dichloro-1-silabutane

i) In the same apparatus and method as in Example 1), aluminum chloride, 1.1 g (0.008 mol) and ortho-xylene, 27 g (0.26 mo1) was added to a round-bottomed flask and allyldichlorosilane, 12.0 g (0.085), was added through a dropping funnel. mol) was added dropwise in an ice bath for 30 minutes and stirred for 1 hour. The completion of the reaction was confirmed by GC, NaCl, 2.4g (0.04mole) was added and the reaction temperature was raised to 50 ℃ and stirred for 30 minutes to remove the activity of the catalyst. Vacuum distillation (95-98 ° C./0.6 mmHg) in the reaction mixture to give 3- (3,4-dimethylphenyl) -1,1-dichloro-1-silabutane and 3- (2,3-dimethylphenyl) -1, 17.8 g (85%) of a product having 1-dichloro-1-silabutane present as 5: 1 was obtained.

ii) Using the same equipment and method as i) above, add 15.8 g (0.149 mole) of meta-xylene, aluminum chloride, 0.65 g (0.005 mol) to a round bottom flask, and add 7.0 g (0.049 g of allyldichlorosilane through a dropping funnel. mol) was added dropwise in an ice bath for 25 minutes and stirred for 1 hour. Thereafter, 1.38 g (0.14 mo1) of NaCl was added thereto, followed by stirring at 50 ° C. for 30 minutes. Vacuum distillation (90-93 ° C./0.6 mmHg) in the reaction mixture to give 3- (2,4-dimethylphenyl) -1,1-dichloro-1-silabutane and 3- (3,5 一 dimethylphenyl) -1, 0.8 g (73%) of a mixture of 1-dichloro-1-silabutane in a ratio of 2.7: 1, containing a small amount of 3- (2,6-methylphenyl) -1,1-dichloro-1-silabutane Got it.

iii) Para-xylene, 37 g (0.349 mol) and aluminum chloride, 0.9 g (0.007 mol) were added to a round-bottomed flask by the dropping funnel using the same device and method as in i) above, and 10 g (0.07 mol) of allyldichlorosilane. Was added dropwise in an ice bath for 30 minutes and stirred for 1 hour. After that, 1.9 g (0.03 mo1) of NaCl was added thereto, followed by stirring at 50 ° C. for 30 minutes. Vacuum distillation (86-9 ° C./0.6 mmHg) in the reaction mixture gave 3- (2,5-dimethylphenyl) -1,1-dichloro-1-silabutane, 9.1 g (81%).

(Example 3)

Preparation of 3- (ethylphenyl) -1,1-dichloro-1-silabutane

In the same apparatus and method as in Example 1), ethylbenzene, 27g (0.255mole) and aluminum chloride, 1.13g (0.009mol) were added to a round bottom flask, and allyldichlorosilane and 12g (0.085mol) were iced through a dropping funnel. Drop in the bath for 30 minutes and stir for 1 hour. Thereafter, 2.4 g (0.04 mo1) of NaCl was added thereto, followed by stirring at 50 ° C. for 30 minutes. Vacuum distillation (80-4 ° C./0.6 mmHg) in the reaction mixture gave 3- (2-ethylphenyl) -1,1-dichloro-1-silabutane and 3- (4-ethylphenyl) -1,1-dichloro- 16.3 g (78%) of product having 1-silabutane mixed in a ratio of 1: 2 was obtained.

(Example 4)

Preparation of 3- (isopropylphenyl) -1,1-dichloro-1-silabutane

In the same apparatus and method as in Example 1), 12.6 g (0.105 mo1) of isopropylbenzene, aluminum chloride, and 0.46 g (0.0035 mo1) were added to a round-bottom flask, and 5 g (0.035 mol) of allyldichlorosilane through a dropping funnel. Add dropwise for 20 minutes and stir for 1 hour. Vacuum distillation (91-4 ° C./0.6 mmHg) in the reaction mixture to give 3- (3-isopropylphenyl) -1,1-dichloro-1-silabutane and 3- (4-isopropylphenyl) -1,1- 6.5 g (71%) of a product containing dichloro-1-silabutane in a 1: 2 ratio was obtained.

(Example 5)

Preparation of 3- (chlorophenyl) -1,1-dichloro-1-silabutane

In the same apparatus and method as in Example 1), chlorobenzene, 11.6 g (0.105 mole) and aluminum chloride, 0.46 g (0.0035 mol) were added to a round bottom flask, and 5 g (0.035 mo1) of allyldichlorosilane was added through a dropping funnel. It was added dropwise at 25 ℃ and stirred for 1 hour. Thereafter, 1.0 g (0.017 mo1) of NaCl was added thereto, and the resultant was stirred at 50 ° C. for 1 hour. Vacuum distillation (75-8 ° C./0.6 mmHg) in the reaction mixture to give 3- (2-chlorophenyl) -1,1-dichloro-1-silabutane and 3- (4-chlorophenyl) -1,1-dichloro- 5.7 g (63%) of a product obtained by a ratio of 1-silabutane to 1: 1 was obtained. As a byproduct, a small amount of compound was obtained in which two aryldichlorosilanes were added to one chlorobenzene.

(Example 6)

Preparation of 3- (bromophenyl) -1,1-dichloro-1-silabutane

In the same apparatus and method as in Example 1, bromobenzene, 21.98 g (0.14 mole) and aluminum chloride, 0.46 g (0.0035 mo1) were added to a round bottom flask, and 5 g (0.035 mo1) of allyldichlorosilane was added through a dropping funnel. It was added dropwise at 25 ℃ for 20 minutes and stirred for 1 hour. Thereafter, 1.0 g (0.017 mo1) of NaCl was added thereto, and the resultant was stirred at 50 ° C. for 1 hour. Vacuum distillation (93-96 ° C./0.6 mmHg) in the reaction mixture to give 3- (2-bromophenyl) -1,1-dichloro-1-silabutane and 3- (4-bromophenyl) -1,1- 4.6 g (62%) of a product in which the ratio of dichloro-1-silabutane was mixed at 1: 1 was obtained. As a by-product, a small amount of a compound in which two allyldichlorosilanes were added to one molecule of bromobenzene was obtained.

(Example 7)

Preparation of 3- (fluorophenyl) -1,1-dichloro-1-silabutane

In the same apparatus and method as in Example 1, fluorobenzene, 4.03 g (0.043 mol) and aluminum chloride, 0.18 g (0.0014 mo1) was added to a round bottom flask, and allyl dichlorosilane and 2.0 g (0.0014 mo1) were added through a dropping funnel. 10 minutes was added dropwise at room temperature and given for 1 hour. Thereafter, 0.4 g (0.007 mo1) of NaCl was added thereto, and the mixture was stirred at 50 ° C. for 1 hour. Vacuum distillation (93-96 ° C./0.6 mmHg) in the reaction mixture to give 3- (2-fluorophenyl) -1,1-dichloro-1-silabutane and 3- (4-fluorophenyl) -1,1-dichloro- 2.0 g (60%) of a product in which the ratio of 1-silabutane was mixed at 1: 1 was obtained. As a by-product, a small amount of a compound in which two allyldichlorosilanes were added to one molecule of bromobenzene was obtained.

(Example 8)

Preparation of 3- (phenylphenyl) -1,1-dichloro-1-silabutane

In the same apparatus and method as in Example 1, biphenyl, 16.2 g (0.105 mo1), aluminum chloride, 0.46 g (0.0035 mol), hexane and 20 m1 were added to a solvent, and the flask was heated to 50 ° C. using a water bath. Allyldichlorosilane, 5g (0.035mol) was added dropwise for 20 minutes and stirred for 1 hour through the dropping funnel. Thereafter, 1.0 g (0.017 mol) of NaCl was added thereto, and the resultant was stirred at 50 ° C. for 1 hour. Vacuum distillation (134-8 ° C./0.6 mmHg) in the reaction mixture to give 3- (2-phenylphenyl) -1,1-dichloro-1-silabutane and 3- (4-phenylpentyl) -1,1-dichloro- 8.5 g (83%) of the product of 1-silabutane obtained in the ratio of 1: 5 was obtained.

(Example 9)

Preparation of 3- (phenoxyphenyl) -1,1-dichloro-1-silabutane

Diphenyl ether, 17.8 g (0.105 mo1) and aluminum chloride, 0.46 g (0.0035 mo1) were added to a round bottom flask by the same apparatus and method as in Example 1, and the round bottom flask was kept at 35 ° C. to be notified through a funnel. 5 g (0.035 mol) of dichlorosilane was added dropwise for 20 minutes and stirred for 1 hour. Then NaCl, 1.0g (0.017mo1) was added and stirred at 50 ℃ for 1 hour. Vacuum distillation (126-130 ° C./0.6 mmHg) in the reaction mixture to afford 3- (2-phenoxyphenyl) -1,1-dichloro-1-silabutane and 3- (4-phenoxyphenyl) -1,1- The product obtained by the ratio of dichloro-1- silabutane in the ratio of 2: 3. 8.02 g (74%) was obtained. And a small amount of 3- (3-phenoxyphenyl) -1,1-dichloro-l-silabutane was obtained.

(Example 10)

Preparation of 3- (naphthyl) -1,1-dichloro-1-silabutane

In the same apparatus and method as in Example 1, naphthalene, 13.6 g (0.105 mo1) and aluminum chloride, 0.45 g (0.0035 mo1), carbon tetrachloride and 20 m1 in a solvent were placed, and the round bottom flask was subjected to dripping at room temperature. Allyldichlorosilane, 5g (0.035mo1) was added dropwise for 20 minutes and stirred for 1 hour. Then NaCl, 1.0 g (0.0)

17mo1) was added and stirred at 50 ° C for 1 hour. Vacuum distillation (128-132 ° C./0.6 mmHg) in the reaction mixture to give 3- (1-naphthyl) -1,1-dichloro-1-silabutane and 3- (2-naphthyl) -1,1-dichloro- 7.6 g (80%) of a product obtained by a ratio of 1-silabutane to 4: 1 was obtained.

The structure of the new 3-aryl-1,1-dichloro-1-silabutane obtained in the same manner as in the above examples and the results of analysis by nuclear magnetic resonance spectroscopy are shown in Table I.

TABLE ^{1 1} H-NMR data of substituent structure of ³ -aryl-1,1-dichloro- ¹ -silabutane

(Example 11)

Preparation of 3- (methylphenyl) -1,1-dichloro-1-silabutane

Toluene, 9.66g (0.105mo1) and aluminum chloride, 0.20g (0.0015ol) were added to a round bottom flask by the same apparatus and method as in Example 1, and allyltrichlorosilane and 3g (0.021mo1) were added to the ice bath through a dropping funnel. 20 minutes drop and stir for 1 hour. Thereafter, 0.48 g (0.008 mol) of NaCl was added thereto, and the resultant was stirred at 50 ° C. for 1 hour. Vacuum distillation (74-76 ° C./0.6 mmHg) in the reaction mixture gave 3- (2-medylphenyl) -1,1,1-trichloro-1-silabutane and 3- (4-methylphenyl) -1,1, 3.2 g (71%) of a product containing 1-trichloro-1-silabutane in a ratio of 1: 3 was obtained.

(Example 12)

Preparation of 3- (chlorophenyl) -1,1-trichloro-1-silabutane

In the same apparatus and method as in Example 1, chlorobenzene, 5.40 g (0.048 mol) and aluminum chloride, 0.20 g (0.0016 mol) were added to a round bottom flask, and allyldichlorosilane, 3 g (0.025 mo1) Add dropwise for a minute and stir for 1 hour. Thereafter, 0.4 g (0.007 mo1) of NaCl was added thereto, followed by stirring at 50 ° C. for 1 hour. Vacuum distillation (78-80 ° C./0.6 mmHg) in the reaction mixture to give 3- (2-chlorophenyl) -1,1-dichloro-1-silabutane and 3- (4-chlorophenyl) -1,1,1- 3.0 g (65.2%) of products obtained by the ratio of trichloro-1- silabutane at 1: 2 were obtained.

Nuclear magnetic resonance spectroscopy analysis of the structure of the new 3-aryl-1,1,1-trichloro-1-silabutane obtained in the same manner as in Examples 11 and 12 is shown in Table II.

Table ¹ H-NMR data of the structure of the substituent Ⅱ.3- aryl-1-sila-butane to -1, 1, 1-trichloroethane

(Example 13)

Preparation of 3- (methylphenyl) -1-dichloro-1-silabutane

Toluene, 10.00 g (0.109 mol), aluminum chloride, 0.40 g (0.003 mo1) was added to a round bottom flask using the same apparatus and method as in Example 1, and allyl chlorosilane and 2.33 g (0.022 mo1) were added to the ice bath through a dropping funnel. 20 minutes drop and stir for 1 hour. NaCl, 0.48 g (0.008 mo1) was added and stirred at 50 ° C. for 1 hour. Vacuum reaction (60-61 ° C./0.6 mmHg) in the reaction mixture gave 3- (2-methylphenyl) -1-chloro-1-silabutane and 3- (4-methylphenyl) -1-chloro-1-silabutane 1 The product, 1.8g (42%) mixed in the ratio of 2 was obtained.

The structure of the new 3-aryl-1-chloro-1-silabutane obtained in the same manner as in Example 13 and the results of analysis by nuclear magnetic resonance spectroscopy are shown in Table III.

Table III. ¹ H-NMR data of substituent structure of aryl-1-chloro-1-silabutane

Claims (25)

2-arylpropylchlorosilane of the following general formula (III): In the above formula, R and R 'are independently hydrogen, C ₁ -C ₄ alkyl group, phenoxy group, fluoro, chloro, bromo, mercapto, mercaptomethyl group and Ar is a benzene ring, naphthalene ring, biphenyl ring, etc. An aryl group is represented and X ₁ , X ₂ and X ₃ independently represent a hydrogen or chloro group. However, when X ₁ , X ₂ , and X ₃ are all chloro groups, R is hydrogen and R 'is chloro or bromo group, and when R and R' are hydrogen, X ₁ , X ₂ and X ₃ are Except when both are chloro groups and when X ₁ is hydrogen and X ₂ and X ₃ are chloro groups. 2- of the general formula (III) of claim 1, wherein the allylsilanes of the general formula (I) and the allylsilanes of the general formula (II) are subjected to predal-craft reaction with a Lewis acid such as aluminum chloride as a catalyst. Method for preparing arylpropylsilane. Wherein R, R ', X ₁ , X ₂ and X ₃ are as defined in claim 1. The process according to claim 2, wherein the compound of formula (I) is characterized in that R is hydrogen and R 'is a methyl group. The process according to claim 2, wherein the compound of formula (I) is characterized in that R is hydrogen and R 'is an ethyl group. The process according to claim 2, wherein the compound of formula (I) is R is hydrogen and R 'is isopropyl group. The process according to claim 2, wherein the compound of formula (I) is wherein R is hydrogen and R 'is a fluoro, chloro or bromo group. The process according to claim 2, wherein the compound of formula (I) is wherein R is hydrogen and R 'is a phenyl group. The process according to claim 2, wherein the compound of formula (I) is wherein R is hydrogen and R 'is a phenoxy group. The process according to claim 2, wherein the compound of formula (I) is R is hydrogen and R 'is a mercapto group (-SH). The process according to claim 2, wherein the compound of formula (I) is R is hydrogen and R 'is a mercaptomethyl group (-CH ₂ SH). The method according to claim 2, wherein the compound of the general formula (I) is characterized in that R and R 'are C ₁ -C ₃ alkyl groups. The process according to claim 2, wherein the compound of formula (II) is X ₁ is hydrogen and X ₂ and X ₃ are chloro groups. The method according to claim 2, wherein the compound of formula (II) is characterized in that X ₁ and X ₂ and X ₃ are both chloro groups. The process according to claim 2, wherein the compound of formula (II) is X ₁ and X ₂ are hydrogen and X ₃ is a chloro group. The compound of formula (III) wherein R is hydrogen, R 'is as defined in claim 1 and is in the 2, 3, 4 position of the phenyl ring and X ₁ is hydrogen and X ₂ and The manufacturing method characterized by the fact that X <_3> is a chloro group. The compound of formula (III) according to claim 2, wherein R is hydrogen and R 'is as defined in claim ₁ and is in positions 2, 3, 4 of the phenyl ring and X ₁ and X ₂ and X ₃ Wherein all are chloro groups. The compound of formula (III) wherein R is hydrogen, R 'is as defined in claim 1 and is in the 2, 3, 4 position of the phenyl ring and X ₁ and X ₂ are hydrogen. The manufacturing method characterized by the fact that X <_3> is a chloro group. The method according to claim 2, wherein the compound of the general formula (III) is characterized in that R and R 'are alkyl groups up to C ₁ -C ₃ , X ₁ is hydrogen and X ₂ and X ₃ are chloro groups. The process according to claim 2, wherein the compound of the general formula (III) is R and R 'are alkyl groups of up to C ₁ -C ₃ and X ₁ , X ₂ and X ₃ are all chloro groups. The method according to claim 2, wherein the compound of formula (III) is characterized in that R and R 'are alkyl groups up to 1 C ₁ -C ₃ , X ₁ and X ₂ are hydrogen and X ₃ is a chloro group. The process according to claim 2, wherein the compound of formula III is R-Ar-R 'is naphthalene, X ₁ is hydrogen and X ₂ and X ₃ are chloro groups. The method according to claim 2, wherein the compound of formula (III) is characterized in that R-Ar-R 'is naphthalene and X ₁ and X ₂ and X ₃ are both chloro groups. The process according to claim 2, wherein the compound of formula III is R-Ar-R 'is naphthalene, X ₁ and X ₂ are hydrogen and X ₃ is a chloro group. The process according to claim 2, wherein the reaction temperature is from 0 deg. 3. A process according to claim 2, wherein aluminum chloride, the reaction catalyst, is used at 1-20% by weight relative to allylchlorosilane.