CN102050837A - Method for synthesizing tri(m-ethoxyphenyl)bismuthine - Google Patents
Method for synthesizing tri(m-ethoxyphenyl)bismuthine Download PDFInfo
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- CN102050837A CN102050837A CN2009102197598A CN200910219759A CN102050837A CN 102050837 A CN102050837 A CN 102050837A CN 2009102197598 A CN2009102197598 A CN 2009102197598A CN 200910219759 A CN200910219759 A CN 200910219759A CN 102050837 A CN102050837 A CN 102050837A
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- Prior art keywords
- phenelyl
- synthesizing
- synthetic
- sodium hydroxide
- bismuths
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- 0 Bc1cc(*)ccc1 Chemical compound Bc1cc(*)ccc1 0.000 description 7
- MNOJRWOWILAHAV-UHFFFAOYSA-N Oc1cccc(Br)c1 Chemical compound Oc1cccc(Br)c1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 2
- YHTLDRWIEYOWCU-UHFFFAOYSA-N Bc1cc(O)ccc1 Chemical compound Bc1cc(O)ccc1 YHTLDRWIEYOWCU-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for synthesizing tri(m-ethoxyphenyl)bismuthine, relates to a method for synthesizing triphenylbismuth derivatives, in particular to a method for synthesizing tri(m-ethoxyphenyl)bismuthine. The method for synthesizing tri(m-ethoxyphenyl)bismuthine has the advantages of simpleness in operation, high yield and favorability of industrialized production. The method comprises the steps of: synthesizing m-bromophenetole; synthesizing m-ethoxyphenyl magnesium bromide; and synthesizing the tri(m-ethoxyphenyl)bismuthine.
Description
Technical field:
The present invention relates to the synthetic method of triphenyl bismuth derivative, more particularly, relate to the synthetic method of three phenelyl bismuths.
Background technology:
Triphenyl bismuth compounds is one of starting material in space rocket, the guided missile composite solidpropellant, is commonly used for the catalyzer of composite solidpropellant, synthesizes to reach also to have in the chemical material preparation process at medicine and quotes application comparatively widely.
Three phenelyl bismuths, chemical formula are C
24H
27Bi O
3, structural formula is as shown below.
Three phenelyl bismuths
Present stage, still at the experimental stage to synthesizing of three phenelyl bismuths, do not carry out industrialized production.
Summary of the invention:
The present invention is exactly at the problems referred to above, provide a kind of simple to operate, productive rate is high, be beneficial to the synthetic method of three phenelyl bismuths of suitability for industrialized production.
In order to realize above-mentioned purpose of the present invention, the present invention adopts following technical scheme, and method steps of the present invention is:
1. a Bromoethyl phenyl ether is synthetic
The sodium hydroxide that in the 100ml three-necked bottle of electric mixer, reflux condensing tube and dropping funnel is housed, adds 30ml water and 0.15mol, bromophenol and tetrabutylammonium iodide between adding then, add-on is, n (bromophenol): n (sodium hydroxide)=2: 3～1: 1, n (tetrabutylammonium iodide): n (sodium hydroxide)=0.04: 1～0.06: 1 adds monobromethane 5～10ml under 60～80 ℃ of stirrings; Behind reaction 2～2.5h, cooling is told organic phase, the water extracted with diethyl ether; Merge organic phase, and use the 10%NaOH solution washing, wash with water then, use anhydrous sodium sulfate drying to being neutral; Steaming desolventizes, and 130～135 ℃ cut is collected in underpressure distillation again, obtains Bromoethyl phenyl ether between colourless liquid;
Reaction equation is:
2. a phenelyl magnesium bromide is synthetic
Reaction equation is:
3. three phenelyl bismuths is synthetic
Reaction equation is:
Beneficial effect of the present invention:
1. step of the present invention is few, and aftertreatment is easy, is beneficial to suitability for industrialized production;
2. productive rate of the present invention is 61.2%.
Embodiment:
Method steps of the present invention is:
1. a Bromoethyl phenyl ether is synthetic
The sodium hydroxide that in the 100ml three-necked bottle of electric mixer, reflux condensing tube and dropping funnel is housed, adds 30ml water and 0.15mol, bromophenol and tetrabutylammonium iodide between adding then, add-on is, n (bromophenol): n (sodium hydroxide)=2: 3～1: 1, n (tetrabutylammonium iodide): n (sodium hydroxide)=0.04: 1～0.06: 1 adds monobromethane 5～10ml under 60～80 ℃ of stirrings; Behind reaction 2～2.5h, cooling is told organic phase, the water extracted with diethyl ether; Merge organic phase, and use the 10%NaOH solution washing, wash with water then, use anhydrous sodium sulfate drying to being neutral; Steaming desolventizes, and 130～135 ℃ cut is collected in underpressure distillation again, obtains Bromoethyl phenyl ether between colourless liquid;
Reaction equation is:
2. a phenelyl magnesium bromide is synthetic
Reaction equation is:
3. three phenelyl bismuths is synthetic
Reaction equation is:
The structure of three phenelyl bismuths of synthetic of the present invention has obtained the affirmation of infrared spectrum and ultimate analysis, and spectral data is as follows:
Ultimate analysis, C
24H
27BiO
3, measured value (calculated value), %:C 50.41 (50.35); H 4.77 (4.75).
In the IR spectrum of compound, at 3032.1cm
-1The absorption peak at place belongs to the stretching vibration of phenyl ring C--H, and 2983.6,2927.1,2882.9cm
-1The absorption peak at place belongs to the stretching vibration of ethyl C-H, and 1574.9,1465.2cm
-1The absorption peak at place belongs to the skeletal vibration peak of phenyl ring, and 1224.1,1050.3cm
-1The absorption peak at place belongs to the stretching vibration absorption peak of aromatic oxide, and 774.0,692.1cm
-1The absorption peak at place belongs to the dibasic vibration absorption peak in position between phenyl ring, 432.4cm
-1The absorption peak at place belongs to the stretching vibration of Bi-C, and the result who measures with X-ray diffraction fits like a glove.
Claims (1)
1. the synthetic method of three phenelyl bismuths is characterized in that, method steps of the present invention is:
(1) Bromoethyl phenyl ether is synthetic between
The sodium hydroxide that in the 100ml three-necked bottle of electric mixer, reflux condensing tube and dropping funnel is housed, adds 30ml water and 0.15mol, bromophenol and tetrabutylammonium iodide between adding then, add-on is, n (bromophenol): n (sodium hydroxide)=2: 3～1: 1, n (tetrabutylammonium iodide): n (sodium hydroxide)=0.04: 1～0.06: 1 adds monobromethane 5～10ml under 60～80 ℃ of stirrings; Behind reaction 2～2.5h, cooling is told organic phase, the water extracted with diethyl ether; Merge organic phase, and use the 10%NaOH solution washing, wash with water then, use anhydrous sodium sulfate drying to being neutral; Steaming desolventizes, and 130～135 ℃ cut is collected in underpressure distillation again, obtains Bromoethyl phenyl ether between colourless liquid;
Reaction equation is:
(2) the phenelyl magnesium bromide is synthetic between
Reaction equation is:
Synthesizing of (3) three phenelyl bismuths
Reaction equation is:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102197598A CN102050837A (en) | 2009-11-11 | 2009-11-11 | Method for synthesizing tri(m-ethoxyphenyl)bismuthine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009102197598A CN102050837A (en) | 2009-11-11 | 2009-11-11 | Method for synthesizing tri(m-ethoxyphenyl)bismuthine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102050837A true CN102050837A (en) | 2011-05-11 |
Family
ID=43955681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2009102197598A Pending CN102050837A (en) | 2009-11-11 | 2009-11-11 | Method for synthesizing tri(m-ethoxyphenyl)bismuthine |
Country Status (1)
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| CN (1) | CN102050837A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105131041A (en) * | 2015-09-15 | 2015-12-09 | 湖南大学 | Novel triphenyl organic bismuth (V) complex catalyst, preparation method thereof, and catalysis application thereof in nitrogen-containing compounds |
| CN108997091A (en) * | 2018-07-10 | 2018-12-14 | 盐城市胜达化工有限公司 | A kind of method of silver bicarbonate activation 2- Bromoethyl phenyl ether |
-
2009
- 2009-11-11 CN CN2009102197598A patent/CN102050837A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105131041A (en) * | 2015-09-15 | 2015-12-09 | 湖南大学 | Novel triphenyl organic bismuth (V) complex catalyst, preparation method thereof, and catalysis application thereof in nitrogen-containing compounds |
| CN105131041B (en) * | 2015-09-15 | 2018-10-09 | 湖南大学 | A kind of catalytic applications in novel triphenyl organo-bismuth (V) composition catalyst and preparation method thereof and nitrogenous compound synthesis |
| CN108997091A (en) * | 2018-07-10 | 2018-12-14 | 盐城市胜达化工有限公司 | A kind of method of silver bicarbonate activation 2- Bromoethyl phenyl ether |
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Application publication date: 20110511 |