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Water heating synthesis of diaryl ether

A technology of diaryl ether and synthetic method, which is applied in ether preparation, organic chemistry, etc., can solve the problems that hinder the application of high-throughput biological activity screening, long reaction time, and difficult handling, so as to improve environmental friendliness and reaction time The effect of shortening and shortening the reaction time

Inactive Publication Date: 2005-10-12
SUN YAT SEN UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

The adverse reaction of organic solvents to the environment, especially the difficulty of post-reaction treatment of aprotic polar solvents and the need for inert gas protection (CN1462735A) in some reaction processes have not been well resolved. On the other hand, the reaction takes a long time It also seriously hinders the application of high-throughput biological activity screening in the current drug and pesticide research and development process
[0004] U.S. Patent US4620046 and European Patent EP1013635 have successively reported the synthesis method of diaryl ether in aqueous medium, but still need to add a large amount of organic solvents

Method used

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  • Water heating synthesis of diaryl ether
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Experimental program
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Embodiment 1

[0022] Embodiment 1: the synthesis of 4-nitrophenylphenyl ether

[0023] 101mg (0.5mmol) 4-nitrobromobenzene, 56.4mg (0.6mmol) phenol, 104mg (0.75mmol) K 2 CO 3 , 32mg (0.1mmol) TBAB, 1.5ml H 2 O was added to an 8ml microwave reaction tube, and reacted at 100W and 110°C for 10min. After the reaction stopped, it was extracted with ethyl acetate, washed with water, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure, separated and purified by silica gel column chromatography [eluent: petroleum ether / ethyl acetate ( 10:1)], 82 mg of 4-nitrophenylphenyl ether was obtained, and the yield was 70%.

[0024] product 1 H NMR (CDCl 3 , 300MHz) δ7.00(m, 2H), 7.08(2, 2H), 7.24(t, J=7.8Hz, 1H), 7.42(t, J=7.8Hz, 2H), 8.18(m, 2H).

Embodiment 2

[0025] Embodiment 2: the synthesis of 4-nitrophenyl-4'-chlorophenyl ether

[0026] 101mg (0.5mmol) 4-nitrobromobenzene, 128mg (1mmol) p-chlorophenol, 11mg (0.05mmol) CoAc 2 4H 2 O, 26.2 mg (0.1 mmol) PPh 3 , 104 mg (0.75 mmol) K 2 CO 3 , 32mg (0.1mmol) TBAB, 1.5ml H 2 O was added to an 8ml microwave reaction tube, and reacted at 100W and 170°C for 20min. After the reaction stopped, it was extracted with ethyl acetate, washed with water, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure, separated and purified by silica gel column chromatography [eluent: petroleum ether / ethyl acetate ( 10:1)] to obtain 115 mg of 4-nitrophenyl-4'-chlorophenyl ether with a yield of 92%.

[0027] product 1 H NMR (CDCl 3 , 300MHz) δ7.01 (m, 4H), 7.38 (d, J=8.7, 2H), 8.20 (d, J=9.3, 2H).

Embodiment 3

[0028] Embodiment 3: the synthesis of phenylphenyl ether

[0029] With 79mg (0.5mmol) bromobenzene, 94mg (1mmol) phenol, 20mg (0.1mmol) PdAc 2 , 12mg (0.1mmol) TMEDA, 104mg (0.75mmol) K 2 CO 3 , 32mg (0.1mmol) TBAB, 1.5ml H 2O was added to an 8ml microwave reaction tube, and reacted at 100W and 190°C for 90min. After the reaction stopped, it was extracted with ethyl acetate, washed with water, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure, separated and purified by silica gel column chromatography [eluent: petroleum ether] to obtain phenyl Phenyl ether 31 mg, yield 37%.

[0030] product 1 H NMR (CDCl 3 , 300MHz) δ6.98 (m, 4H), 7.07 (m, 2H), 7.30 (m, 4H).

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Abstract

Synthesis of diaryl ether in water phase is characterized by taking aryl halogenide and phenol as raw material, taking water as solvent, auxiliarily heating by micro-wave, taking carbonate, fluoride, borate and hydroxide of alkali metal or alkaline earth metal as alkali, and C-O coupling reacting under transition metal catalyzing condition or without transition metal catalyzing condition, with ligand or without ligand, with surface activator or without surface activator. It achieves short reacting time, simple operation, easy separation and good reacting environment.

Description

technical field [0001] The invention relates to a method for synthesizing diaryl ether, in particular to a method for synthesizing diaryl ether with aryl substituents such as aryl halides and phenol by using water as a solvent under microwave-assisted heating conditions. technical background [0002] Diaryl ethers are a very important class of compounds that widely exist in natural and non-natural products with physiological activities. Some diaryl ethers have good biological activity and have even been used as clinical drugs, such as perrottetins, riccardin B, marchantin quinine that affect blood coagulation; the antiviral cyclic peptide K-13; the glycopeptide (glycopeptide) antibiotics Vancomycin (Vancomycin element), Teicoplanin, Complestatin. In recent years, diaryl ethers have been widely used in pesticide research, especially in the creation of new pesticides. The introduction of diaryl ether structures into pesticide molecules can significantly improve the physical a...

Claims

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Application Information

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IPC IPC(8): C07C41/01C07C43/263C07C43/29C07C205/38
Inventor 万一千朱新海王金龙陈功马彦宋化灿许遵乐
Owner SUN YAT SEN UNIV
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