CN105481738B - A kind of method of the copper catalysis synthesis trifluoroethyl thioether of aromatic hydrocarbons 2,2,2 - Google Patents
A kind of method of the copper catalysis synthesis trifluoroethyl thioether of aromatic hydrocarbons 2,2,2 Download PDFInfo
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- CN105481738B CN105481738B CN201610048828.3A CN201610048828A CN105481738B CN 105481738 B CN105481738 B CN 105481738B CN 201610048828 A CN201610048828 A CN 201610048828A CN 105481738 B CN105481738 B CN 105481738B
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
Abstract
The invention discloses a kind of method that copper catalysis synthesizes 2,2,2 trifluoroethyl thioethers：Using cuprous iodide as catalyst, diimine is bidentate ligand, aromatic hydrocarbons halogen, sulphur powder and 2,2,2 trifluoro iodoethane are reactant, sodium borohydride is reducing agent, in N, N solvent dimethylformamides, stirred 1 24 hours at 80 95 DEG C, reaction terminates rear reaction solution and post-processes to obtain 2,2,2 trifluoroethyl sulfide compounds.The advantages that synthetic method of the present invention has catalyst cheap and easy to get and small toxicity, raw material are easy to get, easy to operate, and functional group's universality is good.
Description
Technical field
The invention belongs to organic synthesis field, and in particular to a kind of copper catalysis synthesis trifluoroethyl thioether of aromatic hydrocarbons 2,2,2-
Method.
Background technology
Fluoro-containing group has strong electron-withdrawing and high lipophilic, shows many very unique physical properties and chemically
Matter.After introducing fluoro-containing group into molecule, it can significantly change the polarity of molecule, reduce PKa values and improve membrane permeability, simultaneously
Also the metabolic pathway and Pharmacokinetic Characteristics of molecule be have impact on.In numerous fluoro-containing group compounds, containing 2,2,2- trifluoro second
Sulfur-based compound receives concern especially, contains the group in many has bioactive molecule.However, to being at present
Only, the few of the method report of the trifluoroethyl thioether of aromatic hydrocarbons 2,2,2- is synthesized, mainly passes through aromatic hydrocarbons thiophenol and 2,2,2- trifluoros
The reaction of ethyl alkyl halide obtains.But because aromatic hydrocarbons thiophenol is not easy to obtain, expensive, and there is strong stink, therefore invent a kind of sharp
With some be easy to get, the method for the cheap trifluoroethyl thioether of Material synthesis aromatic hydrocarbons 2,2,2-, there is important application value.
The content of the invention
It is an object of the invention to provide a kind of method of copper catalysis synthesis trifluoroethyl thioether of aromatic hydrocarbons 2,2,2-, the method are former
Expect cheap and easy to get, yield is high, and the adaptability of functional group is fine, and its operation is easy, has good prospects for commercial application.
To achieve the above object, the present invention adopts the following technical scheme that：
A kind of method of the copper catalysis synthesis trifluoroethyl thioether of aromatic hydrocarbons 2,2,2-, using cuprous iodide as catalyst, diimine
For bidentate ligand, aromatic hydrocarbons halogen, sulphur powder and 2,2,2- trifluoro iodoethane are reactant, and sodium borohydride is reducing agent, in N, N-
Reacted in solvent dimethylformamide and the trifluoroethyl thioether of aromatic hydrocarbons 2,2,2- is made, chemical equation is：
。
The structural formula of described aromatic hydrocarbons halogen is：, X is Br or I, the described trifluoroethyl of aromatic hydrocarbons 2,2,2-
The structural formula of thioether is：, R is any one in following formula 1- formulas 39：
The structural formula of described diimine is：, wherein, R1And R2Independent is selected from H or alkyl.
Described cuprous iodide, diimine part, aromatic hydrocarbons halogen, sulphur powder, 2,2,2- trifluoros iodoethane and sodium borohydride
Mol ratio is 0.1-1: 0.1-1:1:1-3:1-3:2-4.
Preferably, described cuprous iodide, diimine part, aromatic hydrocarbons halogen, sulphur powder, 2,2,2- trifluoro iodoethane and boron hydrogen
The mol ratio for changing sodium is 0.1:0.2:1:2:2:3.
The preparation method of the aromatic hydrocarbons 2,2,2- trifluoroethyl thioethers specifically includes following steps：
Into the container with magnetic stirring apparatus add cuprous iodide, diimine part, aromatic hydrocarbons halogen, sulphur powder, 2,2,
2- trifluoros iodoethane, sodium borohydride and DMF, plug is shut after well mixed, puts it into 80-95 DEG C of oil
Continue to stir 1-24 hours in bath, extracted with ether, merge organic phase, with distillation water washing 3 times, organic phase anhydrous magnesium sulfate
Dry, filtering, then revolving removes organic solvent；Obtained crude product is entered by silica gel column chromatography by eluant, eluent of pentane
Row elution, obtains the trifluoroethyl thioether of aromatic hydrocarbons 2,2,2-.
The beneficial effects of the present invention are：
The present invention with industrial aromatic hydrocarbons halogen cheap and easy to get, sulphur powder, 2,2,2- trifluoro iodoethane etc. for raw material, with iodate
It is cuprous to synthesize the trifluoroethyl thioether of aromatic hydrocarbons 2,2,2- for catalyst, universal higher yield is obtained, the adaptability of functional group is fine,
And its operation is easy, has good prospects for commercial application.
Embodiment
In order that content of the present invention easily facilitates understanding, with reference to embodiment to of the present invention
Technical scheme is described further, but the present invention is not limited only to this.
Embodiment 1
In nitrogen atmosphere, polytetrafluoroethylene (PTFE) magnetite one is put into a reactor, adds 0.050 mmol iodine
Change cuprous, 0.10 mmol 1,10- Phens, 0.50 mmol 2- iodo-benzoic acid methyl esters, 1.0 mmol sulphur powders, 1.0
Mmol 2,2,2- trifluoro iodoethane, 1.5 mmol sodium borohydrides, 5 mL DMFs are eventually adding, closed
In system after 80 DEG C of h of stirring reaction 16, room temperature is cooled to, is extracted 3 times with ether, 10 mL, merges organic phase, with distillation every time
Water washing 3 times, organic phase is dried with anhydrous magnesium sulfate, filtering, and then revolving removes organic solvent；Obtained crude product passes through silicon
Plastic column chromatography, eluted by eluant, eluent of pentane, obtain 2- (2,2,2- trifluoro ethylmercapto group) methyl benzoate（Separate yield
83%）.1H NMR (400 MHz, CDCl3) δ 7.96 (d, J = 8.6 Hz, 1H), 7.59 – 7.42 (m, 2H),
7.36 – 7.29 (m, 1H), 3.96 (s, 3H), 3.60 (q, J= 9.7 Hz, 2H). 19F NMR (376 MHz,
CDCl3) δ -65.2 (t, J = 9.7 Hz, 3F)。GC-MS m/z 250 (M+)。
Embodiment 2
In nitrogen atmosphere, polytetrafluoroethylene (PTFE) magnetite one is put into a reactor, adds 0.050 mmol iodine
Change cuprous, 0.10 mmol 1,10- Phens, 0.50 mmol 2- cyano group iodobenzenes, 1.0 mmol sulphur powders, 1.0 mmol 2,
2,2- trifluoro iodoethane, 1.5 mmol sodium borohydrides, 5 mL DMFs are eventually adding, 80 in enclosed system
After DEG C h of stirring reaction 16, room temperature is cooled to, is extracted 3 times with ether, 10 mL, merges organic phase every time, with distillation water washing 3
Secondary, organic phase is dried with anhydrous magnesium sulfate, filtering, and then revolving removes organic solvent；Obtained crude product passes through silica gel column layer
Analysis, is eluted by eluant, eluent of pentane, obtains 2- (2,2,2- trifluoro ethylmercapto group) benzonitrile（Separate yield 76%）.1H
NMR (400 MHz, CDCl3) δ 7.77 – 7.65 (m, 2H), 7.60 (t, J= 7.7 Hz, 1H), 7.45 (t,J= 7.8 Hz, 1H), 3.58 (q, J = 9.5 Hz, 2H). 19F NMR (376 MHz, CDCl3) δ -66.1 (t,J = 9.4 Hz, 3F)。GC-MS m/z 217 (M+)。
Embodiment 3
In nitrogen atmosphere, polytetrafluoroethylene (PTFE) magnetite one is put into a reactor, adds 0.050 mmol iodine
Change cuprous, 0.10 mmol 1,10- Phens, 0.50 mmol 1- iodine naphthalenes, 1.0 mmol sulphur powders, 1.0 mmol 2,2,2-
Trifluoro iodoethane, 1.5 mmol sodium borohydrides, 5 mL DMFs are eventually adding, 85 DEG C are stirred in enclosed system
After mixing 16 h of reaction, room temperature is cooled to, is extracted 3 times with ether, 10 mL, merges organic phase every time, with water washing is distilled 3 times, has
Machine is mutually dried with anhydrous magnesium sulfate, filtering, and then revolving removes organic solvent；Obtained crude product by silica gel column chromatography, with
Pentane is that eluant, eluent is eluted, and obtains 1- (2,2,2- trifluoroethyl) naphthalene thioether（Separate yield 92%）.1H NMR (400
MHz, CDCl3) δ 8.52 (d, J = 8.5 Hz, 1H), 7.91 (m, 3H), 7.63 (m, 2H), 7.48 (t,J = 7.7 Hz, 1H), 3.49 (q, J = 9.7 Hz, 2H). 19F NMR (376 MHz, CDCl3) δ -66.0
(t, J = 9.8 Hz, 3F)。GC-MS m/z 242 (M+)。
Embodiment 4
In nitrogen atmosphere, polytetrafluoroethylene (PTFE) magnetite one is put into a reactor, adds 0.050 mmol iodine
Change cuprous, 0.10 mmol 1,10- Phens, 0.50 mmol 4- iodanisols, 1.0 mmol sulphur powders, 1.0 mmol 2,
2,2- trifluoro iodoethane, 1.5 mmol sodium borohydrides, 5 mL DMFs are eventually adding, 85 in enclosed system
After DEG C h of stirring reaction 16, room temperature is cooled to, is extracted 3 times with ether, 10 mL, merges organic phase every time, with distillation water washing 3
Secondary, organic phase is dried with anhydrous magnesium sulfate, filtering, and then revolving removes organic solvent；Obtained crude product passes through silica gel column layer
Analysis, is eluted by eluant, eluent of pentane, obtains 4- (2,2,2- trifluoro ethylmercapto group) methyl phenyl ethers anisole（Separate yield 84%）.1H
NMR (400 MHz, CDCl3) δ 7.50 (d, J = 8.8 Hz, 2H), 6.89 (d, J = 8.8 Hz, 2H),
3.83 (s, 3H), 3.34 (q, J = 9.8 Hz, 2H). 19F NMR (376 MHz, CDCl3) δ -66.3 (t, J
= 9.8 Hz, 3F)。GC-MS m/z 222 (M+)。
Embodiment 5
In nitrogen atmosphere, polytetrafluoroethylene (PTFE) magnetite one is put into a reactor, adds 0.050 mmol
Cuprous iodide, 0.10 mmol 1,10- Phens, 0.50 mmol 4- tert-butyl group iodobenzenes, 1.0 mmol sulphur powders, 1.0
Mmol 2,2,2- trifluoro iodoethane, 1.5 mmol sodium borohydrides, 5 mL DMFs are eventually adding, closed
In system after 90 DEG C of h of stirring reaction 16, room temperature is cooled to, is extracted 3 times with ether, 10 mL, merges organic phase, with distillation every time
Water washing 3 times, organic phase is dried with anhydrous magnesium sulfate, filtering, and then revolving removes organic solvent；Obtained crude product passes through silicon
Plastic column chromatography, eluted by eluant, eluent of pentane, obtain 4- (2,2,2- trifluoroethyl) tert-butyl benzene thioether（Separate yield
66%）.1H NMR (400 MHz, CDCl3) δ 7.49 (d, J = 7.1 Hz, 2H), 7.41 (d, J = 7.2 Hz,
2H), 3.46 (q, J = 9.7 Hz, 2H), 1.37 (d, J = 1.4 Hz, 9H).19F NMR (376 MHz,
CDCl3) δ -66.3 (t, J = 9.7 Hz, 3F)。GC-MS m/z 248 (M+)。
Embodiment 6
In nitrogen atmosphere, polytetrafluoroethylene (PTFE) magnetite one is put into a reactor, adds 0.050 mmol iodine
Change cuprous, 0.10 mmol 1,10- Phens, 0.50 mmol 4- nitro iodobenzenes, 1.0 mmol sulphur powders, 1.0 mmol 2,
2,2- trifluoro iodoethane, 1.5 mmol sodium borohydrides, 5 mL DMFs are eventually adding, 80 in enclosed system
After DEG C h of stirring reaction 16, room temperature is cooled to, is extracted 3 times with ether, 10 mL, merges organic phase every time, with distillation water washing 3
Secondary, organic phase is dried with anhydrous magnesium sulfate, filtering, and then revolving removes organic solvent；Obtained crude product passes through silica gel column layer
Analysis, is eluted by eluant, eluent of pentane, obtains 4- (2,2,2- trifluoroethyl) nitro diphenyl sulfide（Separate yield 99%）.1H
NMR (400 MHz, CDCl3) δ 8.20 (d, J = 8.9 Hz, 2H), 7.54 (d, J = 8.9 Hz, 2H),
3.63 (q, J = 9.4 Hz, 2H). 19F NMR (376 MHz, CDCl3) δ -66.1 (t, J = 9.4 Hz,
3F)。GC-MS m/z 236 (M+)。
Embodiment 7
In nitrogen atmosphere, polytetrafluoroethylene (PTFE) magnetite one is put into a reactor, adds 0.050 mmol iodine
Change cuprous, 0.10 mmol 1,10- Phens, 0.50 mmol 3- nitro iodobenzenes, 1.0 mmol sulphur powders, 1.0 mmol 2,
2,2- trifluoro iodoethane, 1.5 mmol sodium borohydrides, 5 mL DMFs are eventually adding, 85 in enclosed system
After DEG C h of stirring reaction 16, room temperature is cooled to, is extracted 3 times with ether, 10 mL, merges organic phase every time, with distillation water washing 3
Secondary, organic phase is dried with anhydrous magnesium sulfate, filtering, and then revolving removes organic solvent；Obtained crude product passes through silica gel column layer
Analysis, is eluted by eluant, eluent of pentane, obtains 3- (2,2,2- trifluoroethyl) nitro diphenyl sulfide（Separate yield 87%）.1H
NMR (400 MHz, CDCl3) δ 8.35 (s, 1H), 8.18 (dd, J = 8.2, 2.1 Hz, 1H), 7.81 (d,J = 7.8 Hz, 1H), 7.55 (t, J = 8.0 Hz, 1H), 3.56 (q, J = 9.4 Hz, 2H). 19F NMR
(376 MHz, CDCl3) δ -66.2 (t, J = 9.4 Hz, 3F)。GC-MS m/z 236 (M+)。
Embodiment 8
In nitrogen atmosphere, polytetrafluoroethylene (PTFE) magnetite one is put into a reactor, adds 0.050 mmol iodine
Change cuprous, 0.10 mmol 1,10- Phens, 0.50 mmol 4- cyano group iodobenzenes, 1.0 mmol sulphur powders, 1.0 mmol 2,
2,2- trifluoro iodoethane, 1.5 mmol sodium borohydrides, 5 mL DMFs are eventually adding, 80 in enclosed system
After DEG C h of stirring reaction 16, room temperature is cooled to, is extracted 3 times with ether, 10 mL, merges organic phase every time, with distillation water washing 3
Secondary, organic phase is dried with anhydrous magnesium sulfate, filtering, and then revolving removes organic solvent；Obtained crude product passes through silica gel column layer
Analysis, is eluted by eluant, eluent of pentane, obtains 4- (2,2,2- trifluoroethyl) cyano group diphenyl sulfide（Separate yield 93%）.1H
NMR (400 MHz, CDCl3) δ 7.62 (d, J = 8.5 Hz, 2H), 7.50 (d, J = 8.5 Hz, 2H),
3.57 (q, J = 9.4 Hz, 2H). 19F NMR (376 MHz, CDCl3) δ -66.1 (t, J = 9.4 Hz,
3F)。GC-MS m/z 216 (M+)。
Embodiment 9
In nitrogen atmosphere, polytetrafluoroethylene (PTFE) magnetite one is put into a reactor, adds 0.050 mmol iodine
Change cuprous, 0.10 mmol 1,10- Phens, 0.50 mmol 4- chloroiodobenzones, 1.0 mmol sulphur powders, 1.0 mmol 2,2,
2- trifluoro iodoethane, 1.5 mmol sodium borohydrides, 5 mL DMFs are eventually adding, 80 DEG C in enclosed system
After the h of stirring reaction 16, room temperature is cooled to, is extracted 3 times, every time 10 mL with ether, merges organic phase, with distillation water washing 3 times,
Organic phase is dried with anhydrous magnesium sulfate, filtering, and then revolving removes organic solvent；Obtained crude product by silica gel column chromatography,
Eluted by eluant, eluent of pentane, obtain 4- (2,2,2- trifluoro ethylmercapto group) chlorobenzene（Separate yield 90%）.1H NMR
(400 MHz, CDCl3) δ 7.46 (d, J = 8.5 Hz, 2H), 7.33 (d, J = 8.5 Hz, 2H), 3.43
(q, J = 9.6 Hz, 2H). 19F NMR (376 MHz, CDCl3) δ -66.3 (t, J = 9.6 Hz, 3F)。GC-
MS m/z 226 (M+)。
Embodiment 10
In nitrogen atmosphere, polytetrafluoroethylene (PTFE) magnetite one is put into a reactor, adds 0.050 mmol iodine
Change cuprous, 0.10 mmol 1,10- Phens, 0.50 mmol 4- methyl iodobenzenes, 1.0 mmol sulphur powders, 1.0 mmol 2,
2,2- trifluoro iodoethane, 1.5 mmol sodium borohydrides, 5 mL DMFs are eventually adding, 90 in enclosed system
After DEG C h of stirring reaction 16, room temperature is cooled to, is extracted 3 times with ether, 10 mL, merges organic phase every time, with distillation water washing 3
Secondary, organic phase is dried with anhydrous magnesium sulfate, filtering, and then revolving removes organic solvent；Obtained crude product passes through silica gel column layer
Analysis, is eluted by eluant, eluent of pentane, obtains 4- (2,2,2- trifluoro ethylmercapto group) toluene（Separate yield 83%）.1H NMR
(400 MHz, CDCl3) δ 7.43 (d, J = 8.1 Hz, 2H), 7.17 (d, J = 7.9 Hz, 2H), 3.42
(q, J = 9.8 Hz, 2H), 2.38 (s, 3H). 19F NMR (376 MHz, CDCl3) δ -66.4 (t, J =
9.8 Hz, 3F)。GC-MS m/z 205 (M+)。
Embodiment 11
In nitrogen atmosphere, polytetrafluoroethylene (PTFE) magnetite one is put into a reactor, adds 0.050 mmol iodine
Change cuprous, 0.10 mmol 1,10- Phens, 0.50 mmol 4- bromo nitrobenzenes, 1.0 mmol sulphur powders, 1.0 mmol
2,2,2- trifluoro iodoethane, 1.5 mmol sodium borohydrides, 5 mL DMFs are eventually adding, in enclosed system
After 95 DEG C of h of stirring reaction 1, room temperature is cooled to, is extracted 3 times with ether, 10 mL, merges organic phase every time, with distillation water washing 3
Secondary, organic phase is dried with anhydrous magnesium sulfate, filtering, and then revolving removes organic solvent；Obtained crude product passes through silica gel column layer
Analysis, is eluted by eluant, eluent of pentane, obtains 4- (2,2,2- trifluoro ethylmercapto group) nitrobenzene（Separate yield 99%）.1H
NMR (400 MHz, CDCl3) δ 8.20 (d, J = 8.9 Hz, 2H), 7.54 (d, J = 8.9 Hz, 2H),
3.63 (q, J = 9.4 Hz, 2H). 19F NMR (376 MHz, CDCl3) δ -66.1 (t, J = 9.4 Hz,
3F)。GC-MS m/z 236 (M+)。
Embodiment 12
In nitrogen atmosphere, polytetrafluoroethylene (PTFE) magnetite one is put into a reactor, adds 0.050 mmol iodine
Change cuprous, 0.10 mmol 1,10- Phens, 0.50 mmol 4- bromoanisoles, 1.0 mmol sulphur powders, 1.0 mmol 2,
2,2- trifluoro iodoethane, 1.5 mmol sodium borohydrides, 5 mL DMFs are eventually adding, 95 in enclosed system
After DEG C h of stirring reaction 24, room temperature is cooled to, is extracted 3 times with ether, 10 mL, merges organic phase every time, with distillation water washing 3
Secondary, organic phase is dried with anhydrous magnesium sulfate, filtering, and then revolving removes organic solvent；Obtained crude product passes through silica gel column layer
Analysis, is eluted by eluant, eluent of pentane, obtains 4- (2,2,2- trifluoro ethylmercapto group) methyl phenyl ethers anisole（Separate yield 81%）.1H
NMR (400 MHz, CDCl3) δ 7.50 (d, J = 8.8 Hz, 2H), 6.89 (d, J= 8.8 Hz, 2H),
3.83 (s, 3H), 3.34 (q, J = 9.8 Hz, 2H). 19F NMR (376 MHz, CDCl3) δ -66.3 (t, J
= 9.8 Hz, 3F)。GC-MS m/z 222 (M+)。
The foregoing is only presently preferred embodiments of the present invention, all equivalent changes done according to scope of the present invention patent with
Modification, it should all belong to the covering scope of the present invention.
Claims (3)
- A kind of 1. method of the copper catalysis synthesis trifluoroethyl thioether of aromatic hydrocarbons 2,2,2-, it is characterised in that：Using cuprous iodide as catalysis Agent, diimine are bidentate ligand, and aromatic hydrocarbons halogen, sulphur powder and 2,2,2- trifluoro iodoethane are reactant, using sodium borohydride as also Former agent, reacted in DMF solvent and the trifluoroethyl thioether of aromatic hydrocarbons 2,2,2- is made, described aromatic hydrocarbons halogen Structural formula is：, X is Br or I；The structural formula of described aromatic hydrocarbons 2,2,2- trifluoroethyl thioethers is：；The structural formula of the diimine is：, wherein, R1And R2Independent is selected from H or alkyl；Iodate Cuprous, diimine, aromatic hydrocarbons halogen, sulphur powder, the mol ratio of 2,2,2- trifluoros iodoethane and sodium borohydride are 0.1:0.2:1:2:2: 3。
- 2. a kind of method of copper catalysis synthesis trifluoroethyl thioether of aromatic hydrocarbons 2,2,2- according to claim 1, its feature exist In：R in aromatic hydrocarbons halogen structural formula is any one in following formula 1- formulas 34：。
- 3. synthetic method according to claim 1, it is characterised in that：Comprise the following steps that：To with magnetic stirring apparatus Container in add cuprous iodide, diimine, aromatic hydrocarbons halogen, sulphur powder, 2,2,2- trifluoros iodoethane, sodium borohydride and N, N- diformazan Base formamide, plug is shut after well mixed, puts it into 80-95 DEG C of oil bath and continue to stir 1-24 hours, extracted with ether, Merge organic phase, with water washing is distilled 3 times, organic phase is dried with anhydrous magnesium sulfate, filtering, and then revolving removes organic solvent； Obtained crude product is eluted by eluant, eluent of pentane by silica gel column chromatography, obtains the trifluoroethyl sulphur of aromatic hydrocarbons 2,2,2- Ether.
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| A General and Efficient Approach to Aryl Thiols: CuI-Catalyzed Coupling of Aryl Iodides with Sulfur and Subsequent Reduction;Yongwen Jiang等;《organic letters》;20090930;第11卷(第22期);第5250-5253页 * |
| An Air-Stable Copper Reagent for Nucleophilic Trifluoromethylthiolation of Aryl Halides;Zhiqiang Weng等;《angew.chem.int.ed.》;20131231;第52卷;第1548-1552页 * |
| SRN1 reactions of 2,2,2-trifluoroethyl halides with thiolate ions;zheng-Yu long等;《Journal of fluorine chemistry》;19981231;第91卷;第95-98页 * |
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