A kind of synthetic method of methyl phenyl sulfoxide

A technology of methyl sulfoxide and synthesis method, applied in the synthesis of methyl sulfoxide compounds and the field of synthesis of methyl sulfoxide compounds, can solve the problems of restricting wide application, low efficiency, increased cost, etc., and achieve simple and reasonable process conditions , fast reaction speed and good conversion rate

Active Publication Date: 2019-09-27
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The preparation of methyl sulfoxide compounds with hydrogen peroxide is less polluting and conforms to the concept of "green chemistry", but it needs to prepare auxiliary catalysts in advance, such as DSA@MNPs, which increases additional costs and is not efficient, and uses highly oxidizing metal compounds And although halogen compounds are direct and efficient, their potential toxicity and danger limit their wide application

Method used

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  • A kind of synthetic method of methyl phenyl sulfoxide
  • A kind of synthetic method of methyl phenyl sulfoxide
  • A kind of synthetic method of methyl phenyl sulfoxide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add (10ml) acetonitrile, 885mg (2.50mmol) F-TEDA-BFI solution in a 25ml anhydrous and oxygen-free flask, and add phenyl methyl sulfide (2.0 ml) pre-dissolved in 1.0ml acetonitrile dropwise under a nitrogen atmosphere. mmol), then stirred at room temperature for 10 min, and then added 347 uL (2.5 mmol) of triethylamine, and continued stirring for 10 min. After the reaction, the reaction solution was poured into water, 15ml of dichloromethane was added for extraction, and then Na 2 CO 3 The solution was dried and filtered to obtain methyl phenyl sulfoxide with a yield of 54%

[0032] NMR 1H (CDCl3, 300MHz): δ2.72 (s, 3H), 7.49-7.55 (3H), 7.63-7.66 (2H)

[0033] NMR 13C(CDCl3,100MHz): δ145.4(Cq), 130.8(CH), 129.2(CH), 123.3(CH), 43.7(CH3)

[0034] GCMS(EI)Calcd.for C 7 H 8 OS 140.20,found 140.04.

Embodiment 2

[0036] Add (12ml) acetonitrile, 885mg (2.50mmol) F-TEDA-BFI solution in a 25ml anhydrous and oxygen-free bottle. Under a nitrogen atmosphere, add dropwise methyl-p-toluene sulfide (2.0 mmol), then stirred at room temperature for 10 min, and then added 347 uL (2.5 mmol) of triethylamine, and continued stirring for 10 min. After the reaction, the reaction solution was poured into water, 15ml of dichloromethane was added for extraction, and then Na 2 CO 3 The solution was dried and filtered to obtain methyl p-toluene sulfoxide with a yield of 61%.

[0037] NMR 1H (CDCl3, 400MHz): δ2.41 (s, 3H), 2.70 (s, 3H), 7.32 (d, J = 8.1 Hz, 2H), 7.53 (d, J = 8.1 Hz, 2H)

[0038] NMR 13C (CDCl3, 100MHz): δ142.3 (Cq), 141.5 (Cq), 130.0 (CH), 123.5 (CH), 43.8 (CH3), 21.3 (CH3)

[0039] GCMS(EI)Calcd.for C 8 H 10 OS 154.23, found 154.05.

Embodiment 3

[0041] Add (10ml) acetonitrile and 886mg (2.50mmol) F-TEDA-BFI solution in a 25ml anhydrous and oxygen-free bottle. Under a nitrogen atmosphere, add 4-chlorophenylmethylsulfur pre-dissolved in 1.0ml acetonitrile dropwise Ether (i.e. p-chloroanisole) (2.0 mmol), then stirred at room temperature for 10 min, and then added 350 uL (2.5 mmol) triethylamine, and continued stirring for 10 min. After the reaction, the reaction solution was poured into water, 15ml of dichloromethane was added for extraction, and then Na 2 CO 3 The solution was dried and filtered to obtain p-chlorophenyl methyl sulfoxide with a yield of 68%.

[0042] 1HNMR(500MHz,CDCl3)δ(ppm): 7.63-7.60(m,2H),7.55-7.52(m,2H),2.74(s,3H);

[0043] 13C NMR (126MHz, CDCl3) δ (ppm): 144.2, 137.3, 131.1, 129.7, 128.9, 125.0, 44.0.

[0044] GCMS(EI)Calcd.for C 7 H 7 ClOS 174.64, found 173.99.

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Abstract

The invention discloses a synthesizing method of methyl phenyl sulfoxide. The method is characterized in that a thioanisole derivate is used as a raw material, under nitrogen condition, acetonitrile is used as a solvent, and SelectFluor TM is used as an oxidizing reagent, the reaction is performed for 10-20min at room temperature, then triethylamine is added for continuously catalyzing for 10-20min; the reacting liquid is separated and purified to obtain a dimethyl sulfoxide compound after the reaction is finished. According to the synthesizing method, technical conditions are mild, the operation is simple, the reaction time is extremely short, conversion rate and yield are stable, and the substrate range is wide; the SelectFluor TM is used as the oxidizing reagent, so that a metal catalyst is saved, and the method is an efficient method for synthesizing the dimethyl sulfoxide compound.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a method for synthesizing a methyl sulfoxide compound, and more specifically, to a method for synthesizing a methyl sulfoxide compound from a phenyl methyl sulfide derivative as a raw material. Background technique [0002] Sulfoxide is not only a commonly used solvent and extractant in organic synthesis experiments, it is also widely used in the synthesis of various drugs, and is an important intermediate for medicines, pesticides and expensive materials. The choice of catalyst to efficiently oxidize sulfide to sulfoxide has always been a hot spot in the synthesis field. Currently, the commonly used catalysts mainly include hydrogen peroxide, metal compounds and halogen compounds. [0003] Literature 1. (Zhou,Wenjie et al. Preparation and application of heterogeneousglutamic acid catalyst for aqueous oxidation of sulfide.Faming ZhuanliShenqing,105498836,20Apr 2016) reported a p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/02C07C317/14
Inventor 熊笳妤梁帅帅易文斌储玲
Owner NANJING UNIV OF SCI & TECH
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