CN110981768A

CN110981768A - Simple synthesis method of aryl difluoroalkyl sulfoxide compound

Info

Publication number: CN110981768A
Application number: CN201911338291.4A
Authority: CN
Inventors: 李新进; 刘河甫; 王中一
Original assignee: Shandong University of Technology
Current assignee: Shandong University of Technology
Priority date: 2019-12-23
Filing date: 2019-12-23
Publication date: 2020-04-10

Abstract

The invention particularly relates to a simple synthesis method of an aryl difluoroalkyl sulfoxide compound, belonging to the technical field of organic compound process application. Containing difluoromethylene (-CF)₂-) is an important drug and bioactive molecule, and difluoromethylene is used as a bioisostere of oxygen atom and carbonyl group, has good metabolic stability, and has been widely applied to design of drugs and bioactive molecules. The invention overcomes the defects of the prior art, and firstly proposes the adoption of simple and easily obtained aryl difluoromethyl sulfoxide (ArSOCF) on the basis of the research of predecessors₂H) Is a difluoroalkylating reagent, which is carried out with a haloalkane by means of a base in the absence of metalThe difluorine reaction provides a new method for simply and efficiently synthesizing the aryl difluoroalkyl sulfoxide compound.

Description

Simple synthesis method of aryl difluoroalkyl sulfoxide compound

Technical Field

The invention particularly relates to a novel simple synthesis method of an aryl difluoroalkyl sulfoxide compound, which utilizes aryl difluoromethyl sulfoxide as a difluoroalkylation reagent to realize a difluoroalkylation reaction of halogenated alkanes (bromine and iodoalkane), and belongs to the technical field of organic compound process application.

Background

The organic fluorine-containing compound shows unique physical properties, chemical reactivity and physiological activity due to introduction of fluorine, and is more and more widely applied in the fields of medicines, pesticides, functional materials and the like. The development of novel fluorine-containing reagents and novel fluorine (alkylation) processes is therefore of great importance. The compound containing difluoromethylene is an important bioactive molecule or a drug molecule precursor, and the introduction of difluoroalkyl can improve the metabolic stability of biomolecules, so that the application value and the research significance are very high. Sulfinyl is also different from other sulfur moieties because the sulfur atom in this oxidation state has a lone electron pair, resulting in the formation of a chiral center at the sulfur atom, which plays an important role in drugs such as omprazole, Lansoprazole, etc. As shown in fig. 1. Therefore, the synthesis of the aryl difluoroalkyl sulfoxide compound has important theoretical research significance and potential application value.

The prior art is as follows: (1) nucleophilic fluoroalkylation of difluoromethyl phenyl sulfone with halohydrocarbon under the action of potassium tert-butoxide. The difluoroalkylation product can be subjected to elimination reaction under the action of alkali to generate geminal difluoroolefin, and can also be subjected to desulfonyl under the action of Na/Hg to obtain a product. (Prakash, G.K. S.; Hu, J.; Wang, Y.; Olah, G.A.).Angew. Chem. Int. Ed. 2004, 43, 5203；Prakash, G. K. S.; Hu, J.; Wang, Y.;Olah, G. A.Org. Lett.2004, 6, 4315.）

(2) Under the action of alkali, phenyl difluoro methyl sulfoxide and aldehyde and ketone are subjected to nucleophilic addition reaction, so that the alcohol compound containing difluoro sulfinyl is synthesized. (Zhu L, Li Y, Ni C, et al.J. Fluorine Chem..2007, 128(10): 1241.）。

Disclosure of Invention

The invention overcomes the defects of the prior art, and utilizes the simple and easily obtained aryl difluoromethyl sulfoxide (ArSOCF) for the first time on the basis of the research of the predecessor₂H) The method is a fluoroalkyl reagent, realizes the difluorinated reaction with halogenated alkane under the action of alkali, and provides a new method for simply and efficiently realizing the synthesis of the aryl difluoroalkyl sulfoxide compound.

As shown in FIG. 2, the present invention utilizes aryl difluoromethyl sulfoxide (ArSOCF)₂H) And halogenated alkane are taken as raw materials, and the aryl difluoroalkyl sulfoxide compound is obtained by reaction in a proper solvent under the action of hexamethyldisilazane based potassium amide (KHMDS).

Wherein Ar is an aryl group.

In the invention, the dosage ratio of the

starting materials

1 and 2 is 1:1-1: 3. Preferably, the ratio of the two is 1: 2.

In the present invention, the base is hexamethyldisilazane (KHMDS) or hexamethyldisilazane (LiHMDS).

Preferably, the base is potassium hexamethyldisilazide (KHMDS).

In the present invention, the solvent is N, N-Dimethylformamide (DMF). Wherein the solvent is used in an amount of 1.5 ml.

In the present invention, the reaction temperature is-20 deg.C^oC。

In the invention, the reaction time is 2 h.

In the invention, the concentrations of the aryl difluoromethyl sulfoxide, the halogenated alkane and the hexamethyldisilazane in N, N-dimethylformamide are as follows in sequence: 0.2M, 0.4M.

Specifically, the synthesis method of the invention comprises the steps of adding reactant 1 (0.2 mmol), reactant 2 (0.4 mmol) and 1.5ml of DMF solution into a 10ml Schlenk reaction tube, and placing the reaction system in a nitrogen atmosphere at-20%^oC, stirring, adding KHMDS (0.4 mmol,1M in THF) dropwise at the temperature, and continuing the reaction at the temperature for 2h after the addition. After the reaction is finished, detecting the reaction by TLC, and carrying out column chromatography separation to obtain a target product 3.

The advantages of the synthetic product of the invention include: the raw materials used by the synthetic method are very cheap, the properties are very stable, and special storage is not needed. The alkali used in the invention is also a common commercial reagent, is very stable, and has the characteristics of low cost, high yield, simple process and less pollution.

The synthesis method of the aryl difluoroalkyl sulfoxide compound is a very potential fluorine-containing modification method for bioactive molecules, and a reaction route innovatively designed by the invention provides a widely applicable synthesis method for modifying the compound.

The invention takes aryl difluoromethyl sulfoxide and halogenated alkane as reactants to react to obtain the aryl difluoroalkyl sulfoxide compound. The method has the advantages of simple operation, mild reaction conditions and high yield, and is suitable for large-scale production.

Drawings

Figure 1 is two drug molecules omeprazole and lansoprazole.

FIG. 2 is a reaction formula of the synthesis method.

FIG. 3 is (4, 4-difluoro-4- (phenylsulfinyl) butyl) benzene.

FIG. 4 is ((1, 1-difluoroheptyl) sulfinyl) benzene.

FIG. 5 is ((1, 1-difluoropentyl) sulfinyl) benzene.

FIG. 6 is ((1, 1-difluoropropyl) sulfinyl) benzene.

FIG. 7 is ((1, 1-difluoropropyl) sulfinyl) benzene.

FIG. 8 is ((1, 1-difluorononyl) sulfinyl) benzene.

FIG. 9 is (4, 4-difluoro-4- (phenylsulfinyl) butoxy) benzene.

FIG. 10 is ((5, 5-difluoro-5- (phenylsulfinyl) pentyl) oxy) benzene.

FIG. 11 is 1- ((5, 5-difluoro-5- (phenylsulfinyl) pentyl) oxy) -4-methoxybenzene.

Figure 12 is 3- ((5, 5-difluoro-5- (benzenesulfinyl) pentyl) oxy) benzonitrile.

FIG. 13 is 1- (tert-butyl) -4- ((5, 5-difluoro-5- (phenylsulfinyl) pentyl) oxy) benzene.

FIG. 14 is 1-chloro-4- ((5, 5-difluoro-5- (phenylsulfinyl) pentyl) oxy) benzene.

FIG. 15 is ((1, 1-difluorohex-5-en-1-yl) sulfinyl) benzene.

FIG. 16 is 1- ((1, 1-difluoropentyl) sulfinyl) -4-fluorobenzene.

FIG. 17 is 1- ((1, 1-difluoro-4-phenylbutyl) sulfinyl) -4-fluorobenzene.

FIG. 18 is 1- ((1, 1-difluoro-4-phenoxybutyl) sulfinyl) -4-fluorobenzene.

FIG. 19 is 1- (tert-butyl) -4- ((5, 5-difluoro-5- ((4-fluorophenyl) sulfinyl) pentyl) oxy) benzene.

FIG. 20 is 3- ((5, 5-difluoro-5- ((4-fluorophenyl) sulfinyl) pentyl) oxy) benzonitrile.

FIG. 21 is 1- ((1, 1-difluoropentyl) sulfinyl) -4-methoxybenzene.

FIG. 22 is 1- ((1, 1-difluoro-4-phenylbutyl) sulfinyl) -4-methoxybenzene.

FIG. 23 is 1- ((1, 1-difluoro-4-phenoxybutyl) sulfinyl) -4-methoxybenzene.

Detailed Description

The present invention will be described in further detail with reference to the following specific examples, but the present invention is not limited to the following examples. Variations and advantages that may occur to those skilled in the art may be incorporated into the invention without departing from the spirit and scope of the inventive concept, and the scope of the appended claims is intended to be protected. The procedures, conditions, reagents, experimental methods and the like for carrying out the present invention are general knowledge and common general knowledge in the art except for the contents specifically mentioned below, and the present invention is not particularly limited. The data given in the examples below include specific operating and reaction conditions and products. The product structure is determined by nuclear magnetic resonance (¹H NMR，¹⁹F NMR，¹³C NMR) identification.

Example 1

FIG. 3

(4, 4-difluoro-4- (phenylsulfinyl) butyl) benzene (3 a)

To a 10ml Schlenk reaction tube were added phenyldifluoromethyl sulfoxide (0.2 mmol, 35.2 mg), 1-bromo-3-phenylpropane (0.4 mmol) and 1.5ml of DMF solution, and the reaction system was placed under a nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, the TLC detection reaction is carried out, and column chromatography separation is carried out to obtain the target product 3a (72%).¹H NMR (400 MHz , CDCl₃): δ 7.68 (d,J= 8.0 Hz , 2H) , 7.60-7.52 (m, 3H) , 7.27 (t,J= 8.0 Hz , 2H) , 7.19 (t,J=8.0 Hz , 1H) , 7.13 (d,J= 8.0 Hz , 2H) , 2.65 (t ,J= 8.0 Hz , 2H) , 2.37-2.19 (m, 1H) , 2.03-1.79 (m, 3H).¹⁹F NMR (376 MHz, CDCl₃): δ -101.80 (1F,ddd,² J _FF= 221.8 Hz,³ J _FH= 26.3, 11.3 Hz, CF₂CH₂), -104.04 (1F, ddd,² J _FF=221.8 Hz,³ J _FH= 26.3, 7.5 Hz, CF₂CH₂).¹³C NMR (100 MHz, CDCl₃): δ 140.8, 136.8(t,³ J _CF= 2.7 Hz), 132.3, 129.1, 128.4, 128.3, 128.2 (dd,¹ J _CF= 296.0, 284.0Hz), 126.1, 125.8, 35.0, 29.5 (t,² J _CF= 20.2 Hz), 22.9 (t,³ J _CF= 3.3 Hz)。

Example 2

FIG. 4

((1, 1-Difluoroheptyl) sulfinyl) benzene (3b)

To a 10ml Schlenk reaction tube were added phenyldifluoromethyl sulfoxide (0.2 mmol, 35.2 mg), bromon-hexane (0.4 mmol) and 1.5ml of DMF solution, and the reaction system was placed under a nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, detecting the reaction by TLC, and separating by column chromatography to obtain a target product 3b (74% of bromo-n-hexane and 92% of iodo-n-hexane).¹H NMR (400 MHz,CDCl₃): δ 7.64 (d,J= 7.2 Hz, 2H), 7.54-7.47 (m, 3H), 2.28-2.10 (m, 1H),1.91-1.75 (m, 1H), 1.59-1.40 (m, 2H), 1.29-1.16 (m, 6H), 0.80 (t,J= 6.4 Hz,3H).¹⁹F NMR (376 MHz, CDCl₃): δ -102.05 (1F, ddd,² J _FF= 221.8 Hz,³ J _FH= 26.1,12.9 Hz, CF₂CH₂), -104.14 (1F, ddd,² J _FF= 221.8 Hz,³ J _FH= 26.0, 8.1 Hz,CF₂CH₂).¹³C NMR (100 MHz, CDCl₃): δ 136.9 (t,³ J _CF= 2.7 Hz), 132.3, 129.0,128.3 (dd,¹ J _CF= 296.0, 284.0 Hz), 31.3, 30.0 (t,² J _CF= 20.2 Hz), 22.3, 21.0(t,³ J _CF= 3.3 Hz), 13.9。

Example 3

FIG. 5

((1, 1-difluoropentyl) sulfinyl) benzene (3c)

To a 10ml Schlenk reaction tube were added phenyldifluoromethyl sulfoxide (0.2 mmol, 35.2 mg), n-butyl bromide (0.4 mmol) and 1.5ml of DMF solution, and the reaction was placed under a nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, detecting the reaction by TLC, and separating by column chromatography to obtain the target product 3c (72% of n-butyl bromide and 92% of n-butyl iodide).¹H NMR (400 MHz,CDCl₃): δ 7.71 (d,J= 8.0 Hz, 2H), 7.61-7.54 (m, 3H) , 2.36-2.18 (m, 1H) ,1.99-1.83 (m, 1H) , 1.66-1.45 (m, 2H) , 1.42-1.32 (m, 2H) , 0.91 (t,J= 8.0Hz, 3H).¹⁹F NMR (376 MHz, CDCl₃): δ -102.06 (1F, ddd,² J _FF= 221.8 Hz,³ J _FH=26.3, 15.0 Hz, CF₂CH₂), -104.15 (1F, ddd,² J _FF= 221.8 Hz,³ J _FH= 26.3, 7.5 Hz,CF₂CH₂).¹³C NMR (100 MHz, CDCl₃): δ 136.9 (t,³ J _CF= 2.7 Hz), 132.3, 129.0,128.4 (dd,¹ J _CF= 296.0, 284.0 Hz), 125.9, 29.7 (t,² J _CF= 20.2 Hz), 23.1 (t,³ J _CF= 3.3 Hz), 22.2, 13.7。

Example 4

FIG. 6

((1, 1-Difluoropropyl) sulfinyl) benzene (3d)

To a 10ml Schlenk reaction tube was added phenyl difluoromethyl sulfoxide(0.2 mmol, 35.2 mg), bromoethane (0.4 mmol) and 1.5ml of DMF solution under nitrogen atmosphere, the reaction system was placed at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, detecting the reaction by TLC, and separating by column chromatography to obtain the target product 3d (bromoethane 59%, iodoethane 78%).¹H NMR (400 MHz, CDCl₃):δ 7.71 (d,J= 7.2 Hz, 2H), 7.61-7.54 (m, 3H), 2.38-2.21 (m, 1H), 2.04-1.88(m, 1H), 1.11 (t,J= 7.2 Hz, 3H).¹⁹F NMR (376 MHz, CDCl₃): δ -104.27 (1F,ddd,² J _FF= 221.8 Hz,³ J _FH= 25.4, 13.3 Hz, CF₂CH₂), -106.01 (1F, ddd,² J _FF=221.8 Hz,³ J _FH= 25.1, 8.3 Hz, CF₂CH₂₎.¹³C NMR (100 MHz, CDCl₃): δ 136.9 (t,³ J _CF= 2.7 Hz), 132.3, 129.1, 128.5 (dd,¹ J _CF= 295.5, 284.2 Hz), 125.9, 23.7(t,² J _CF= 20.9 Hz), 5.4 (t,³ J _CF= 4.7 Hz)。

Example 5

FIG. 7

((1, 1-Difluoropropyl) sulfinyl) benzene (3e)

To a 10ml Schlenk reaction tube were added phenyldifluoromethyl sulfoxide (0.2 mmol, 35.2 mg), iodomethane (0.4 mmol) and 1.5ml of DMF solution, and the reaction system was placed under a nitrogen atmosphere at-20^oStirring at the temperature, adding KHMDS (0.4 mmol) dropwise at the temperature, and continuing the reaction at the temperature for 2h after the addition is finished. After the reaction is finished, the TLC detection reaction is carried out, and the column chromatography separation is carried out to obtain the target product 3e (40%).¹H NMR (400 MHz, CDCl₃): δ 7.71 (d,J= 7.3 Hz, 2H),7.62-7.55 (m, 3H), 1.74 (t,J=18.4 Hz, 3H).¹⁹F NMR (376 MHz, CDCl₃): δ -93.42 (dq,J= 226.6, 18.6 Hz), -96.71 (dq,J= 226.7, 18.3 Hz).¹³C NMR (100MHz, CDCl₃): δ 132.4, 129.2, 128.3 (dd,¹ J _CF= 290.3, 279.7 Hz), 125.6, 16.4(t,² J _CF= 22.0 Hz)。

Example 6

FIG. 8

((1, 1-Difluorononyl) sulfinyl) benzene (3f)

To a 10ml Schlenk reaction tube were added phenyldifluoromethyl sulfoxide (0.2 mmol, 35.2 mg), bromo-n-octane (0.4 mmol) and 1.5ml of DMF solution, and the reaction system was placed under a nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, the TLC detection reaction is carried out, and the column chromatography separation is carried out to obtain the target product 3f (55%).¹H NMR (400 MHz, CDCl₃): δ 7.70 (d,J= 7.2Hz, 2H), 7.61-7.54 (m, 3H), 2.34-2.17 (m, 1H), 1.97-1.81 (m, 1H), 1.66-1.45(m, 2H), 1.32-1.25 (m, 10H), 0.87 (t,J= 6.0 Hz, 3H).¹⁹F NMR (376 MHz,CDCl₃): δ -102.04 (1F, ddd,² J _FF= 221.8 Hz,³ J _FH= 26.1, 13.0 Hz, CF₂CH₂), -104.14 (1F, ddd,² J _FF= 221.8 Hz,³ J _FH= 26.0, 8.0 Hz, CF₂CH₂).¹³C NMR (100MHz, CDCl₃): δ 136.9 (t,³ J _CF= 2.6 Hz), 132.3, 129.0, 128.3 (dd,¹ J _CF= 295.9,284.0 Hz), 125.9, 31.7, 30.0 (t,² J _CF= 20.2 Hz), 22.6, 21.1 (t,³ J _CF= 3.4Hz), 14.0。

Example 7

FIG. 9

(4, 4-difluoro-4- (phenylsulfinyl) butoxy) benzene (3g)

To a 10ml Schlenk reaction tube were added phenyldifluoromethyl sulfoxide (0.2 mmol, 35.2 mg), (3-bromopropoxy) benzene (0.4 mmol) and 1.5ml of a DMF solution, and the reaction system was placed under a nitrogen atmosphere at-20^oStirring at C, and at this temperature, KHMDS (0.4 mmol,1M in THF) is added dropwiseAfter the addition, the reaction was continued at this temperature for 2 hours. After the reaction is finished, the TLC detection reaction and column chromatography separation are carried out to obtain 3g (53%) of the target product.¹H NMR (400 MHz , CDCl₃): δ 7.73 (d,J= 7.4Hz, 2H) , 7.63-7.56 (m,3H), 7.28 (t,J= 8.0 Hz, 2H), 6.95 (t,J= 7.3 Hz,1H), 6.85 (d,J= 8.3 Hz, 2H), 3.99 (t ,J= 5.8 Hz, 2H), 2.57-2.38 (m, 1H),2.24-1.97 (m, 3H).¹⁹F NMR (376 MHz, CDCl₃): δ -101.88 (1F, ddd,² J _FF=223.2Hz,³ J _FH= 26.2, 11.8 Hz, CF₂CH₂), -104.21 (1F, ddd,² J _FF= 223.1.4 Hz,³ J _FH=27.1, 7.4 Hz, CF₂CH₂).¹³C NMR (100 MHz, CDCl₃): δ 158.5, 136.8 (t,³ J _CF= 2.7Hz), 132.4, 129.5, 129.2, 128.3 (dd,¹ J _CF= 295.4, 283.9 Hz), 125.9, 120.9,114.4, 66.2, 29.7, 27.0 (t,² J _CF= 20.3 Hz), 21.4 (t,³ J _CF= 3.5 Hz)。

Example 8

FIG. 10 shows a schematic view of a

((5, 5-difluoro-5- (phenylsulfinyl) pentyl) oxy) benzene (3h)

To a 10ml Schlenk reaction tube were added phenyldifluoromethyl sulfoxide (0.2 mmol, 35.2 mg), (4-iodobutyloxy) benzene (0.4 mmol) and 1.5ml of a DMF solution, and the reaction system was placed under a nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, detecting the reaction by TLC, and separating by column chromatography to obtain a target product for 3h (58%).¹H NMR (400 MHz , CDCl₃): δ 7.64 (d,J=7.2 Hz, 2H) , 7.54-7.46 (m, 3H) , 7.20 (t,J= 7.3 Hz, 2H) , 6.86 (t,J= 7.3Hz, 1H) , 6.78 (d,J= 8.1 Hz, 2H) , 3.87 (t ,J= 5.4 Hz, 2H) , 2.37-2.20(m, 1H) , 1.99-1.84 (m, 3H), 1.75-1.61 (m, 4H).¹⁹F NMR (376 MHz, CDCl₃): δ -102.09 (1F, ddd,² J _FF= 222.9 Hz,³ J _FH= 26.0, 12.2 Hz, CF₂CH₂), -104.10 (1F,ddd,² J _FF= 222.8 Hz,³ J _FH= 26.3, 8.0 Hz, CF₂CH₂).¹³C NMR (100 MHz, CDCl₃): δ158.7, 136.8 (t,³ J _CF= 2.7 Hz), 132.4, 129.4, 129.1, 128.2 (dd,¹ J _CF= 295.6,284.0 Hz), 125.9, 120.7, 114.4, 67.0, 60.4, 29.6 (t,² J _CF= 20.2 Hz), 28.7,21.0, 18.2 (t,³ J _CF= 3.6 Hz), 14.2。

Example 9

FIG. 11

1- ((5, 5-difluoro-5- (phenylsulfinyl) pentyl) oxy) -4-methoxybenzene (3i)

To a 10ml Schlenk reaction tube were added phenyldifluoromethyl sulfoxide (0.2 mmol, 35.2 mg), 1- (4-bromobutoxy) -4-methoxybenzene (0.4 mmol) and 1.5ml of a DMF solution, and the reaction was placed in a-20 ml Schlenk reaction tube under a nitrogen atmosphere^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, TLC detection reaction and column chromatography separation are carried out to obtain the target product 3i (1- (4-bromobutoxy) -4-methoxybenzene 44%,1- (4-iodobutoxy) -4-methoxybenzene 62%).¹H NMR (400 MHz , CDCl₃): δ 7.71 (d,J= 7.2 Hz,2H) , 7.61-7.53 (m, 3H) , 6.83-6.78 (m, 4H) , 3.89 (t,J= 5.6 Hz, 2H) , 3.76(s, 3H) , 2.43-2.26 (m, 1H) , 2.06-1.90 (m, 1H) , 1.85-1.71 (m, 4H).¹⁹F NMR(376 MHz, CDCl₃): δ -102.08 (1F, ddd,² J _FF= 222.7 Hz,³ J _FH= 26.0, 12.3 Hz,CF₂CH₂), -104.07 (1F, ddd,² J _FF= 222.7 Hz,³ J _FH= 26.2, 8.0 Hz, CF₂CH₂).¹³C NMR(100 MHz, CDCl₃): δ 153.7, 152.9, 136.8 (t,³ J _CF= 2.7 Hz), 132.3, 129.1,128.2 (dd,¹ J _CF= 295.7, 284.2 Hz), 125.8, 115.3, 114.5, 67.7, 55.6, 29.6 (t,² J _CF= 20.2 Hz), 28.7, 18.1 (t,³ J _CF= 3.5 Hz)。

Example 10

FIG. 12

3- ((5, 5-difluoro-5- (benzenesulfinyl) pentyl) oxy) benzonitrile (3j)

To a 10ml Schlenk reaction tube were added phenyldifluoromethyl sulfoxide (0.2 mmol, 35.2 mg), 3- (4-bromobutoxy) benzonitrile (0.4 mmol) and 1.5ml of DMF solution, and the reaction system was placed in-20 under a nitrogen atmosphere^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, the TLC detection reaction and column chromatography separation are carried out to obtain the target product 3j (55 percent of 3- (4-bromobutoxy) benzonitrile and 57 percent of 3- (4-iodobutoxy) benzonitrile).¹H NMR (400 MHz , CDCl₃): δ 7.71 (d,J= 7.4 Hz, 2H) , 7.62-7.54 (m, 3H), 7.35 (t,J= 8.4 Hz, 1H) , 7.22 (d,J= 7.5 Hz, 1H) , 7.08 (d,J= 6.3 Hz,2H) , 3.95 (t,J= 5.5 Hz, 2H) , 2.44-2.27 (m, 1H) , 2.06-1.90 (m, 1H) ,1.88-1.67 (m, 4H).¹⁹F NMR (376 MHz, CDCl₃): δ -102.08 (1F, ddd,² J _FF= 223.3Hz,³ J _FH= 26.1, 12.0 Hz, CF₂CH₂), -104.06 (1F, ddd,² J _FF= 223.4 Hz,³ J _FH=26.5, 7.8 Hz, CF₂CH₂).¹³C NMR (100 MHz, CDCl₃): δ 158.8, 136.7 (t,³ J _CF= 2.6Hz), 132.4, 130.3, 129.1, 128.2 (dd,¹ J _CF= 295.7, 283.9 Hz), 125.8, 124.5,119.6, 118.6, 117.3, 113.1, 67.5, 29.4 (t,² J _CF= 20.3 Hz), 28.4, 18.0 (t,³ J _CF= 3.6 Hz)。

Example 11

FIG. 13

1- (tert-butyl) -4- ((5, 5-difluoro-5- (phenylsulfinyl) pentyl) oxy) benzene (3 k)

To a 10ml Schlenk reaction tube were added phenyldifluoromethyl sulfoxide (0.2 mmol, 35.2 mg), 1- (4-bromobutoxy) -4- (tert-butyl) benzene (0.4 mmol) and 1.5ml of a DMF solution, and the reaction system was placed under a nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, the TLC detection reaction and column chromatography separation obtain the target product 3k (1- (4-bromobutoxy) -4- (tert-butyl) benzene 50%, 1- (4-iodobutyloxy) -4- (tert-butyl) benzene 56%).¹H NMR (400 MHz , CDCl₃): δ 7.71 (d,J= 7.3Hz, 2H), 7.60-7.53 (m, 3H), 7.29 (d,J= 8.4 Hz, 2H) , 6.80 (d,J= 8.4 Hz,2H) , 3.93 (t,J=5.2 Hz, 2H), 2.43-2.27 (m, 1H) , 2.06-1.90 (m, 1H), 1.81-1.71 (m, 4H), 1.29 (s, 9H).¹⁹F NMR (376 MHz, CDCl₃): δ -102.08 (1F, ddd,² J _FF= 222.7 Hz,³ J _FH= 26.0, 12.3 Hz, CF₂CH₂), -104.08 (1F, ddd,² J _FF= 222.7 Hz,³ J _FH= 26.3, 7.9 Hz, CF₂CH₂).¹³C NMR (100 MHz, CDCl₃): δ 156.4, 143.3, 136.8(t,³ J _CF= 2.6 Hz), 132.3, 129.1, 128.2 (dd,¹ J _CF= 295.7, 284.2 Hz), 126.2,125.8, 113.8, 67.0, 34.0, 31.5, 29.6 (t,² J _CF= 20.2 Hz), 28.7, 18.0 (t,³ J _CF=3.6 Hz)。

Example 12

FIG. 14

1-chloro-4- ((5, 5-difluoro-5- (phenylsulfinyl) pentyl) oxy) benzene (3 l)

To a 10ml Schlenk reaction tube were added phenyldifluoromethyl sulfoxide (0.2 mmol, 35.2 mg), 1- (4-bromobutoxy) -4-chlorobenzene (0.4 mmol) and 1.5ml of a DMF solution, and the reaction system was placed in a-20 ml Schlenk reaction tube under a nitrogen atmosphere^oStirring at C, adding KHMDS (0.4 mmol,1M in THF) dropwise at this temperature, and continuing at this temperature after the addition is completeThe reaction is carried out for 2 h. After the reaction, the TLC detection reaction and column chromatography separation were carried out to obtain 3l (54% of 1- (4-bromobutoxy) -4-chlorobenzene, 56% of 1- (4-iodobutyloxy) -4-chlorobenzene) as the target product.¹H NMR (400 MHz , CDCl₃): δ 7.71 (d,J= 7.4 Hz, 2H), 7.62-7.54(m, 3H), 7.21 (d,J= 8.8 Hz, 2H), 6.78 (d,J= 8.8 Hz, 2H), 3.91 (t,J=5.4Hz, 2H), 2.44-2.27 (m, 1H), 2.06-1.90 (m, 1H), 1.82-1.67 (m, 4H).¹⁹F NMR (376MHz, CDCl₃): δ -102.07 (1F, ddd,² J _FF= 223.0 Hz,³ J _FH= 26.0, 12.2 Hz, CF₂CH₂),-104.10 (1F, ddd,² J _FF= 223.0 Hz,³ J _FH= 26.3, 7.9 Hz, CF₂CH₂).¹³C NMR (100MHz, CDCl₃): δ 157.4, 136.8 (t,³ J _CF= 2.7 Hz), 132.4, 129.3, 129.1, 128.2(dd,¹ J _CF= 297.4, 283.9 Hz), 125.9, 125.5, 115.6, 67.4, 29.6 (t,² J _CF= 20.3Hz), 28.6, 18.1 (t,³ J _CF= 3.6 Hz)。

Example 13

FIG. 15 shows a schematic view of a

((1, 1-Difluorohex-5-en-1-yl) sulfinyl) benzene (3m)

To a 10ml Schlenk reaction tube were added phenyldifluoromethyl sulfoxide (0.2 mmol, 35.2 mg), 5-bromopent-1-ene (0.4 mmol) and 1.5ml of DMF solution, and the reaction system was placed under a nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, detecting the reaction by TLC, and separating by column chromatography to obtain a target product 3m (48%).¹H NMR (400 MHz , CDCl₃): δ 7.71 (d,J=7.3 Hz, 2H), 7.61-7.54 (m, 3H), 5.78-5.68 (m, 1H), 5.03-4.98 (m, 2H), 2.36-2.19 (m, 1H), 2.10 (q,J= 7.1 Hz , 2H), 2.01-1.85 (m, 2H), 1.78-1.57 (m,2H).¹⁹F NMR (376 MHz, CDCl₃): δ -101.95 (1F, ddd,² J _FF= 222.2 Hz,³ J _FH= 26.3,12.6 Hz, CF₂CH₂), -104.18 (1F, ddd,² J _FF= 222.2 Hz,³ J _FH= 26.1, 7.9 Hz,CF2CH2).¹³C NMR (100 MHz, CDCl₃): δ 136.9, 136.8 (t,³ J _CF= 2.7 Hz), 132.3,129.0, 128.3 (dd,¹ J _CF= 296.0, 284.1 Hz), 125.8, 32.8, 29.3 (t,² J _CF= 20.2Hz), 20.2 (t,³ J _CF= 3.3 Hz)。

Example 14

FIG. 16

1- ((1, 1-difluoropentyl) sulfinyl) -4-fluorobenzene (3q)

To a 10ml Schlenk reaction tube were added 1- ((difluoromethyl) sulfinyl) -4-fluorobenzene (0.2 mmol, 38.8 mg), n-butyl bromide (0.4 mmol) and 1.5ml of a DMF solution, and the reaction system was placed under a nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, detecting the reaction by TLC, and separating by column chromatography to obtain the target product 3q (61% of n-butyl bromide and 85% of n-butyl iodide).¹HNMR (400 MHz, CDCl₃): δ 7.72 (dd,J= 8.0, 5.3 Hz, 2H), 7.27 (t,J= 8.5 Hz,2H), 2.36-2.19 (m, 1H), 2.04-1.88 (m, 1H), 1.67-1.47 (m, 2H), 1.43-1.34 (m,2H), 0.92 (t,J= 7.2 Hz , 3H).¹⁹F NMR (376 MHz, CDCl₃): δ -102.16 (1F, ddd,² J _FF= 221.2 Hz,³ J _FH= 26.0, 13.5 Hz, CF₂CH₂), -104.71 (1F, ddd,² J _FF= 221.2Hz,³ J _FH= 25.5, 7.9 Hz, CF2CH2), -106.43 (m, 1F).¹³C NMR (100 MHz, CDCl₃): δ166.5, 164.0, 132.2 (q,³ J _CF= 2.8 Hz), 128.4, 128.3, 128.1 (ddd,¹ J _CF=296.9,284.0, 3.0 Hz), 116.7, 116.4, 29.9 (t,² J _CF= 20.2 Hz), 23.1 (t,³ J _CF= 3.1Hz), 22.2, 13.6。

Example 15

FIG. 17

1- ((1, 1-difluoro-4-phenylbutyl) sulfinyl) -4-fluorobenzene (3r)

To a 10ml Schlenk reaction tube were added 1- ((difluoromethyl) sulfinyl) -4-fluorobenzene (0.2 mmol, 38.8 mg), 1-bromo-3-phenylpropane (0.4 mmol) and 1.5ml of a DMF solution, and the reaction system was placed under a nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, the TLC detection reaction is carried out, and column chromatography separation is carried out to obtain the target product 3r (67%).¹H NMR (400 MHz,CDCl₃): δ 7.67 (dd,J= 7.9, 5.3 Hz, 2H), 7.30-7.18 (m, 5H), 7.14 (d,J= 7.5Hz, 2H), 2.67 (t,J= 7.6 Hz, 2H), 2.36-2.20 (m, 1H), 2.06-1.81 (m, 3H).¹⁹FNMR (376 MHz, CDCl₃): δ -101.92 (1F, ddd,² J _FF= 221.8 Hz,³ J _FH= 25.4, 13.6 Hz,CF₂CH₂), -104.59 (1F, ddd,² J _FF= 221.1 Hz,³ J _FH= 25.1, 6.7 Hz, CF₂CH₂), -106.21 (m, 1F).¹³C NMR (100 MHz, CDCl₃): δ 166.5, 164.0, 140.6, 132.1 (q,³ J _CF= 2.8 Hz), 128.5, 128.3, 128.2, 128.0 (ddd,¹ J _CF=296.9, 284.4, 1.5 Hz),126.2, 116.7, 116.5, 35.0, 29.6 (t,² J _CF= 20.2 Hz), 22.8 (t,³ J _CF= 3.2 Hz)。

Example 16

FIG. 18

1- ((1, 1-difluoro-4-phenoxybutyl) sulfinyl) -4-fluorobenzene (3s)

To a 10ml Schlenk reaction tube were added 1- ((difluoromethyl) sulfinyl) -4-fluorobenzene (0.2 mmol, 38.8 mg), (3-bromopropoxy) benzene (0.4 mmol) and 1.5ml of a DMF solution, and the reaction was placed under a nitrogen atmosphere at-20^oStirring at C, adding KHMDS (0.4 mmol,1M in THF) dropwise at the temperature, and continuing to addThe reaction was carried out at this temperature for 2 h. After the reaction is finished, the TLC detection reaction is carried out, and the column chromatography separation is carried out to obtain the target product 3s (51%).¹H NMR (400 MHz, CDCl₃):δ 7.72 (dd,J= 7.8, 5.5 Hz, 2H), 7.30-7.25 (m, 4H), 6.95 (t,J= 7.3 Hz,1H), 6.85 (d,J= 8.2 Hz, 2H), 3.99 (t,J= 5.8 Hz, 2H), 2.56-2.38 (m, 1H),2.28-1.98 (m, 3H).¹⁹F NMR (376 MHz, CDCl₃): δ -101.96 (1F, ddd,² J _FF= 222.6Hz,³ J _FH= 26.1, 11.9 Hz, CF₂CH₂), -104.59 (1F, ddd,² J _FF= 222.6 Hz,³ J _FH=26.7, 7.8 Hz, CF₂CH₂), -106.12 (m, 1F).¹³C NMR (100 MHz, CDCl₃): δ 166.6,164.1, 158.5, 132.1 (q,³ J _CF= 2.8 Hz), 129.5, 128.3, 128.2, 128.0 (ddd,¹ J _CF=296.4, 284.2, 1.7 Hz), 120.9, 116.8, 116.5, 114.4, 66.1, 27.2 (t,² J _CF= 20.4Hz), 21.4 (t,³ J _CF= 3.5 Hz)。

Example 17

FIG. 19

1- (tert-butyl) -4- ((5, 5-difluoro-5- ((4-fluorophenyl) sulfinyl) pentyl) oxy) benzene (3t)

To a 10ml Schlenk reaction tube were added 1- ((difluoromethyl) sulfinyl) -4-fluorobenzene (0.2 mmol, 38.8 mg), 1- (4-bromobutoxy) -4- (tert-butyl) benzene (0.4 mmol) and 1.5ml of a DMF solution, and the reaction was placed under a nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, detecting the reaction by TLC, and separating by column chromatography to obtain the target product 3t (50%).¹H NMR (400MHz, CDCl₃): δ 7.71 (dd,J= 7.9, 5.3 Hz, 2H), 7.36-7.19 (m, 4H), 6.80 (d,J= 8.6 Hz, 2H), 3.94 (t,J= 5.3 Hz, 2H), 2.44-2.27 (m, 1H), 2.11-1.97 (m,1H), 1.83-1.71 (m, 4H), 1.30 (s, 9H).¹⁹F NMR (376 MHz, CDCl₃): δ -102.18 (1F,ddd,² J _FF= 222.4 Hz,³ J _FH= 26.0, 12.8 Hz, CF₂CH₂), -104.62 (1F, ddd,² J _FF=222.2 Hz,³ J _FH= 25.7, 7.9 Hz, CF₂CH₂), -106.17 (m, 1F).¹³C NMR (100 MHz,CDCl₃): δ 166.6, 164.1, 156.4, 143.4, 132.1 (q,³ J _CF= 2.8 Hz), 130.9, 128.3,128.2, 128.0 (dd,¹ J _CF=295.4, 283.0 Hz), 126.2, 116.7, 116.5, 113.8, 67.0,34.0, 31.5, 29.8 (t,² J _CF= 20.2 Hz), 28.7, 18.2 (t,³ J _CF= 3.6 Hz)。

Example 18

FIG. 20

3- ((5, 5-difluoro-5- ((4-fluorophenyl) sulfinyl) pentyl) oxy) benzonitrile (3u)

To a 10ml Schlenk reaction tube were added 1- ((difluoromethyl) sulfinyl) -4-fluorobenzene (0.2 mmol, 38.8 mg), 3- (4-bromobutoxy) benzonitrile (0.4 mmol) and 1.5ml of DMF solution, and the reaction system was placed under a nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, detecting the reaction by TLC, and separating by column chromatography to obtain the target product 3u (63%).¹H NMR (400 MHz,CDCl₃): δ 7.72 (dd,J= 8.0, 5.3 Hz, 2H), 7.37 (t,J= 8.4 Hz, 1H), 7.26 (q,J= 8.3 Hz, 3H), 7.10 (d,J= 6.9 Hz, 1H), 3.98 (t,J= 5.5 Hz, 2H), 2.46-2.29 (m, 1H), 2.13-1.97 (m, 1H), 1.89-1.71 (m, 4H).¹⁹F NMR (376 MHz, CDCl₃):δ -102.14 (1F, ddd,² J _FF= 222.5 Hz,³ J _FH= 26.0, 12.6 Hz, CF₂CH₂), -104.72 (1F,ddd,² J _FF= 222.5 Hz,³ J _FH= 25.8, 7.7 Hz, CF₂CH₂), -106.02 (m, 1F).¹³C NMR(100 MHz, CDCl₃): δ 166.6, 164.0, 158.8, 132.0 (q,³ J _CF= 2.8 Hz), 130.3,128.3, 128.2, 127.9 (dd,¹ J _CF=298.0, 285.0 Hz), 124.5, 119.6, 118.6, 117.2,116.7, 116.5, 113.1, 67.5, 29.7 (t,² J _CF= 20.0 Hz), 28.4, 18.1 (t,³ J _CF= 3.0Hz)。

Example 19

FIG. 21

1- ((1, 1-difluoropentyl) sulfinyl) -4-methoxybenzene (3v)

To a 10ml Schlenk reaction tube were added 1- ((difluoromethyl) sulfinyl) -4-methoxybenzene (0.2 mmol,41.2 mg), n-butyl bromide (0.4 mmol) and a solution of 1.5ml of DMF, and the reaction was placed under a nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, detecting the reaction by TLC, and separating by column chromatography to obtain the target product 3v (n-butyl bromide 68%, n-butyl iodide 64%).¹H NMR (400 MHz, CDCl₃): δ 7.62 (d,J= 8.5 Hz, 2H), 7.04 (d,J= 8.6 Hz,2H), 3.85 (s, 3H), 2.32-2.14 (m, 1H), 2.00-1.83 (m, 1H), 1.64-1.44 (m, 2H),1.40-1.31 (m, 2H), 0.90 (t,J= 7.3 Hz, 3H).¹⁹F NMR (376 MHz, CDCl₃): δ -102.70 (1F, ddd,² J _FF= 221.5 Hz,³ J _FH= 26.2, 12.9 Hz, CF2CH2), -105.28 (1F,ddd,² J _FF= 221.5 Hz,³ J _FH= 25.9, 8.0 Hz, CF₂CH₂).¹³C NMR (100 MHz, CDCl₃): δ163.0, 128.1 (dd,¹ J _CF= 295.1, 283.6 Hz), 127.8, 127.4 (t,³ J _CF= 2.7 Hz),114.6, 55.5, 29.7 (t,² J _CF= 20.3 Hz), 23.1 (t,³ J _CF= 3.3 Hz), 22.2, 13.7。

Example 20

FIG. 22

1- ((1, 1-difluoro-4-phenylbutyl) sulfinyl) -4-methoxybenzene (3w)

To a 10ml Schlenk reaction tube was added 1- (R) (1)Difluoromethyl) sulfinyl) -4-methoxybenzene (0.2 mmol,41.2 mg), 1-bromo-3-phenylpropane (0.4 mmol) and 1.5ml of DMF solution were placed in a reaction system under nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, the TLC detection reaction is carried out, and column chromatography separation is carried out to obtain the target product 3w (69%).¹H NMR (400 MHz ,CDCl₃): δ 7.60 (d,J= 8.5 Hz, 2H), 7.27 (t,J= 7.4 Hz, 2H), 7.19 (t,J=7.2Hz, 1H), 7.13 (d,J= 7.6 Hz, 2H), 7.03 (d,J= 7.6 Hz, 2H), 3.85 (s, 3H),2.65 (t ,J= 7.2 Hz, 2H), 2.34-2.18 (m, 1H), 2.05-1.78 (m, 3H).¹⁹F NMR (376MHz, CDCl₃): δ -102.43 (1F, ddd,² J _FF= 222.0 Hz,³ J _FH= 25.4, 13.0 Hz, CF₂CH₂),-105.16 (1F, ddd,² J _FF= 222.4 Hz,³ J _FH= 24.9, 7.2 Hz, CF₂CH₂).¹³C NMR (100MHz, CDCl₃): δ 163.0, 140.7, 128.4, 128.3, 128.0 (dd,¹J_CF= 295.1, 283.9 Hz),127.8, 127.3 (t,³ J _CF= 2.6 Hz), 126.1, 114.6, 55.5, 35.0, 29.5 (t,²J_CF= 20.4Hz), 22.9 (t,³J_CF= 3.2 Hz)。

Example 21

FIG. 23 shows a schematic view of a display panel

1- ((1, 1-difluoro-4-phenoxybutyl) sulfinyl) -4-methoxybenzene (3x)

To a 10ml Schlenk reaction tube were added 1- ((difluoromethyl) sulfinyl) -4-methoxybenzene (0.2 mmol,41.2 mg), (3-bromopropoxy) benzene (0.4 mmol) and 1.5ml of a DMF solution, and the reaction system was placed under a nitrogen atmosphere at-20^oStirring is carried out at C, KHMDS (0.4 mmol,1M in THF) is added dropwise at this temperature, and after the addition is completed, the reaction is continued for 2h at this temperature. After the reaction is finished, the TLC detection reaction is carried out, and the column chromatography separation is carried out to obtain the target product 3x (32%).¹H NMR (400 MHz ,CDCl₃): δ 7.65 (d,J= 8.5 Hz, 2H), 7.28 (t,J= 7.4 Hz , 2H), 7.06 (d,J=8.6 Hz, 2H), 6.95 (t,J= 7.3 Hz, 1H), 6.85 (d,J= 8.3 Hz, 2H), 3.99 (t ,J= 5.8 Hz, 2H), 3.87 (s,3H), 2.54-2.36 (m, 1H), 2.25-1.97 (m, 3H).¹⁹F NMR (376MHz, CDCl₃): δ -102.51 (1F, ddd,² J _FF= 222.8 Hz,³ J _FH= 26.0, 11.5 Hz, CF₂CH₂),-105.29 (1F, ddd,² J _FF= 222.7 Hz,³ J _FH= 27.0, 7.6 Hz, CF₂CH₂).¹³C NMR (100MHz, CDCl₃): δ 163.1, 158.5, 129.4, 128.1 (dd,¹ J _CF= 294.6, 283.7 Hz), 127.8,127.3 (t,³ J _CF= 2.6 Hz), 120.9, 114.8, 114.4, 66.2, 55.5, 27.0 (t,² J _CF= 20.6Hz), 21.4 (t,³ J _CF= 3.5 Hz)。

Claims

1. An aryl difluoroalkyl sulfoxide compound characterized by having ArSOCF₂-R₁Structure (II) wherein R₁The aliphatic hydrocarbon group is methyl, ethyl, n-butyl, n-hexyl, propylbenzene, phenoxypropyl, phenoxyn-butyl, p-methoxyphenoxy n-butyl, p-chlorophenoxy n-butyl, p-tert-butylphenoxy n-butyl and the like; wherein Ar is: and aromatic (hetero) rings such as phenyl, p-fluorophenyl, p-methoxyphenyl, and the like.

2. A method of synthesizing an aryl difluoroalkyl sulfoxide compound as claimed in claim 1, wherein the aryl difluoromethyl sulfoxide (ArSOCF) is used₂H) Reacting with halogenated alkane (bromine and iodoalkane) at low temperature for 2h by adding alkali and reaction solvent to obtain the aryl difluoroalkyl sulfoxide compound.

3. The method of synthesizing an aryl difluoroalkyl sulfoxide compound of claim 2, wherein the base is potassium hexamethyldisilazide (KHMDS).

4. The method of synthesizing an aryl difluoroalkyl sulfoxide of claim 2, wherein the solvent is N, N-Dimethylformamide (DMF).

5. The method of synthesizing an aryl sulfoxide difluoroalkyl compound of claim 2 wherein the solvent is used in an amount of 1.5 ml.

6. The method of synthesizing an aryl sulfoxide difluoroalkyl compound of claim 2 wherein the reaction temperature is-20 deg.f^oC。

7. The method of synthesizing an aryl sulfoxide difluoroalkyl compound of claim 2 wherein the reaction time is 2 hours.

8. The method of synthesizing an aryl sulfoxide difluoroalkyl compound of claim 2 wherein the concentrations of aryl difluoromethyl sulfoxide, alkyl halide, and potassium hexamethyldisilazide in N, N-dimethylformamide are, in order: 0.2M, 0.4M.