CN109942389A - The preparation method and application of 1,3- bis- (3,4- halogen phenyl) acetone - Google Patents
The preparation method and application of 1,3- bis- (3,4- halogen phenyl) acetone Download PDFInfo
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Abstract
The invention belongs to medical science and field of photovoltaic materials, disclose the preparation method and application of 1,3- bis- (3,4- halogen phenyl) acetone.Fragrant phenylacetic acid reaction preparation 1,3- bis- (3,4- halogen phenyl) acetone that the present invention is replaced using two kinds of halogens.Operation is simple and easy, carries out under mild reaction conditions.Synthetic method provided by the invention is simple and easy, scientific and reasonable, environmentally protective, economical and practical, is suitble to large-scale production.
Description
Technical field
The invention belongs to medical science and field of photovoltaic materials, relate generally to the system of 1,3- bis- (3,4- halogen phenyl) acetone
Preparation Method and application.
Background technique
Diphenyl acetone due to its unique molecular structure, photoelectric characteristic and their applications on p- electronic material,
Make its poromerics, crystallization photoconductor, synthesizing graphite alkene in terms of using more and more extensive.Meanwhile diphenyl
Acetone can be used as a kind of cheap precursor, relative complex structure fast and effeciently be prepared, so in terms of pharmaceutical synthesis
There is important application.Based on this, this field needs easier, green, economic method to synthesize diphenyl acetone.
Summary of the invention
For overcome the deficiencies in the prior art, the present invention provides the preparation methods of 1,3- bis- (3,4- halogen phenyl) acetone
And application.Phenylacetic acid reaction preparation 1,3- bis- (3,4- halogen phenyl) acetone that the present invention is replaced using two kinds of halogens.Reaction behaviour
Make simple and easy, carries out under mild reaction conditions.Simple and easy, scientific and reasonable, the green ring of synthetic method provided by the invention
It protects, is economical and practical, being suitble to large-scale production.
Above-mentioned purpose of the invention is achieved through the following technical solutions:
The preparation method of one kind 1,3- bis- (3,4- halogen phenyl) acetone, using the phenylacetic acid of two kinds of halogens substitution as raw material,
Using DMAP as catalyst, DCC is dehydrating agent, is chemically reacted in organic solvent, finally obtains (3, the 4- halogen benzene of 1,3- bis-
Base) acetone, there is the structure as shown in general formula (I)；
Wherein, R1With R2For identical-Br；
The phenylacetic acid that two kinds of halogens replace is respectively the isophthalic second replaced to phenylacetic acid, halogen that halogen replaces
Acid；
What the halogen replaced is 1:1 to phenylacetic acid molar ratio between phenylacetic acid and halogen substitution；
The molar ratio to phenylacetic acid and DCC that the halogen replaces is 1~3:4~6, the halogen replace to benzene
The molar ratio of acetic acid and DMAP are 2~4:1~2；
The organic solvent is dry methylene chloride；
Dry methylene chloride refers to the methylene chloride after removing water, operates as follows, it may be assumed that methylene chloride is added in flask
And calcium hydride, distillation obtains dry methylene chloride at 60 DEG C.
The molar ratio to phenylacetic acid and dry methylene chloride that the halogen replaces is 1:40~80；The halogen
The molar ratio of phenylacetic acid and dry methylene chloride is 1:90~130 between replacing；
What the halogen replaced is to phenylacetic acid
Phenylacetic acid is between the halogen replaces
Wherein R3With R4For-Br.
Specific step is as follows for preparation method:
S1. phenylacetic acid is added in round-bottomed flask by what DCC, DMAP and halogen replaced, and dry dichloromethane is added
Alkane stirs evenly；
S2. the isophthalic acetic acid that halogen replaces is slowly added dropwise to the reaction solution of step S1 in dichloromethane solution
In, 20~30 DEG C of reaction 24-72h；
S3. it is filtered to remove the precipitating of step S2, obtains (3, the 4- halogen benzene of 1,3- bis- with column Chromatographic purification after filtrate revolving
Base) acetone.
Further, the elution in step S3 column chromatography is that ladder elutes, and is first eluted with petroleum ether, then with acetic acid second
Ester: petroleum ether=1:10 elution.
Further, dry with anhydrous sodium sulfate before the filtrate revolving in the step 3.
Further, the dropwise addition mode of the step S2 is constant pressure funnel dropwise addition.
The DCC is dicyclohexylcarbodiimide, and the DMAP is dimethylamino naphthyridine.
1,3- bis- made from preparation method of the present invention (3,4- halogen phenyl) acetone is in medicine preparation and field of photovoltaic materials
On application.
Such as it is used for antidiabetic drugOr photoelectricity crystallizes conductor material
Preparation.
Compared with the prior art, the invention has the advantages that:
The present invention uses what two kinds of halogens replaced to prepare (the 3,4- halogen of 1,3- bis- to phenylacetic acid and isophthalic acetic acidreaction for the first time
Phenyl) acetone；Operation is simple and easy, is not necessarily to nitrogen protection, can carry out under mild reaction conditions.It is provided by the invention
Synthetic method reaction yield is high, and preparation process is simple, not will cause environmental pollution.Synthetic method provided by the invention is to report for the first time
Road, simple and easy, scientific and reasonable, economical and practical, suitable large-scale production.
Specific embodiment
The present invention is described in detail below by specific embodiment, but is not limited the scope of the invention.Unless otherwise specified, originally
Experimental method used by inventing is conventional method, and experiment equipment used, material, reagent etc. can chemically company be bought.
Embodiment 1
A 100mL round-bottomed flask is taken, by DCC (1.0320g, 5mmol), DMAP (0.1527g, 1.25mmol) and 4- bromine
Phenylacetic acid (0.5376g, 2.5mmol) is added in the dry methylene chloride of 10mL, stirs at 20 DEG C to whole dissolutions.By 3- bromine
Phenylacetic acid (0.5376g, 2.5mmol) is dissolved in the dry methylene chloride of 20mL, is then slowly added dropwise with constant pressure funnel
To in above-mentioned solution.Stirring for 24 hours, is spin-dried for, and then through pillar layer separation, (ladder is eluted, and is first eluted with petroleum ether, then use volume ratio
For ethyl acetate: petroleum ether=1:10) to obtain target compound.
It is characterized as below:
1,3- bis- (3,4- bromophenyl) acetone: yield: 70%, fusing point: 93-95 DEG C.1H NMR(500MHz,CDCl3)δ
7.49-7.45 (m, 2H), 7.43 (d, J=8.0Hz, 1H), 7.32 (s, 1H), 7.22 (t, J=7.8Hz, 1H), 7.10 (d, J=
7.6Hz, 1H), 7.04 (d, J=8.3Hz, 2H), 3.73 (s, 2H), 3.70 (s, 2H)
Embodiment 2
A 100mL round-bottomed flask is taken, by DCC (1.0320g, 5mmol), DMAP (0.1527g, 1.25mmol) and 4- bromine
Phenylacetic acid (0.5376g, 2.5mmol) is added in the dry methylene chloride of 10mL, stirs at 25 DEG C to whole dissolutions.By 3- bromine
Phenylacetic acid (0.5376g, 2.5mmol) is dissolved in the dry methylene chloride of 20mL, is then slowly added dropwise with constant pressure funnel
To in above-mentioned solution.Stirring for 24 hours, is spin-dried for, and then through pillar layer separation, (ladder is eluted, and is first eluted with petroleum ether, then use volume ratio
For ethyl acetate: petroleum ether=1:10) to obtain target compound.
It is characterized as below:
1,3- bis- (3,4- bromophenyl) acetone: yield: 66%, fusing point: 93-95 DEG C.1H NMR(500MHz,CDCl3)δ
7.49-7.45 (m, 2H), 7.43 (d, J=8.0Hz, 1H), 7.32 (s, 1H), 7.22 (t, J=7.8Hz, 1H), 7.10 (d, J=
7.6Hz, 1H), 7.04 (d, J=8.3Hz, 2H), 3.73 (s, 2H), 3.70 (s, 2H)
Embodiment 3
A 100mL round-bottomed flask is taken, by DCC (1.0320g, 5mmol), DMAP (0.1527g, 1.25mmol) and 4- bromine
Phenylacetic acid (0.5376g, 2.5mmol) is added in the dry methylene chloride of 10mL, stirs at 30 DEG C to whole dissolutions.By 3- bromine
Phenylacetic acid (0.5376g, 2.5mmol) is dissolved in the dry methylene chloride of 20mL, is then slowly added dropwise with constant pressure funnel
To in above-mentioned solution.Stirring for 24 hours, is spin-dried for, and then through pillar layer separation, (ladder is eluted, and is first eluted with petroleum ether, then use volume ratio
For ethyl acetate: petroleum ether=1:10) to obtain target compound.
It is characterized as below:
1,3- bis- (3,4- bromophenyl) acetone: yield: 60%, fusing point: 93-95 DEG C.1H NMR(500MHz,CDCl3)δ
7.49-7.45 (m, 2H), 7.43 (d, J=8.0Hz, 1H), 7.32 (s, 1H), 7.22 (t, J=7.8Hz, 1H), 7.10 (d, J=
7.6Hz, 1H), 7.04 (d, J=8.3Hz, 2H), 3.73 (s, 2H), 3.70 (s, 2H)
Embodiment 4
A 100mL round-bottomed flask is taken, by DCC (1.0320g, 5mmol), DMAP (0.1527g, 1.25mmol) and 4- bromine
Phenylacetic acid (0.5376g, 2.5mmol) is added in the dry methylene chloride of 10mL, stirs at 20 DEG C to whole dissolutions.By 3- bromine
Phenylacetic acid (0.5376g, 2.5mmol) is dissolved in the dry methylene chloride of 20mL, is then slowly added dropwise with constant pressure funnel
To in above-mentioned solution.48h is stirred, is spin-dried for, then (ladder elutes, and is first eluted with petroleum ether, then use volume ratio through pillar layer separation
For ethyl acetate: petroleum ether=1:10) to obtain target compound.
It is characterized as below:
1,3- bis- (3,4- bromophenyl) acetone: yield: 60%, fusing point: 93-95 DEG C.1H NMR(500MHz,CDCl3)δ
7.49-7.45 (m, 2H), 7.43 (d, J=8.0Hz, 1H), 7.32 (s, 1H), 7.22 (t, J=7.8Hz, 1H), 7.10 (d, J=
7.6Hz, 1H), 7.04 (d, J=8.3Hz, 2H), 3.73 (s, 2H), 3.70 (s, 2H)
Embodiment 5
A 100mL round-bottomed flask is taken, by DCC (1.0320g, 5mmol), DMAP (0.1527g, 1.25mmol) and 4- bromine
Phenylacetic acid (0.5376g, 2.5mmol) is added in the dry methylene chloride of 10mL, stirs at 20 DEG C to whole dissolutions.By 3- bromine
Phenylacetic acid (0.5376g, 2.5mmol) is dissolved in the dry methylene chloride of 20mL, is then slowly added dropwise with constant pressure funnel
To in above-mentioned solution.72h is stirred, is spin-dried for, then (ladder elutes, and is first eluted with petroleum ether, then use volume ratio through pillar layer separation
For ethyl acetate: petroleum ether=1:10) to obtain target compound.
It is characterized as below:
1,3- bis- (3,4- bromophenyl) acetone: yield: 55%, fusing point: 93-95 DEG C.1H NMR(500MHz,CDCl3)δ
7.49-7.45 (m, 2H), 7.43 (d, J=8.0Hz, 1H), 7.32 (s, 1H), 7.22 (t, J=7.8Hz, 1H), 7.10 (d, J=
7.6Hz, 1H), 7.04 (d, J=8.3Hz, 2H), 3.73 (s, 2H), 3.70 (s, 2H)
Embodiment 6
A 100mL round-bottomed flask is taken, by DCC (0.8247g, 4mmol), DMAP (0.1466g, 1.2mmol) and 4- bromine
Phenylacetic acid (0.5351g, 2.5mmol) is added in the dry methylene chloride of 8mL, stirs at 20 DEG C to whole dissolutions.By 3- bromine
Phenylacetic acid (0.5351g, 2.5mmol) is dissolved in the dry methylene chloride of 18mL, is then slowly added dropwise with constant pressure funnel
To in above-mentioned solution.Stirring for 24 hours, is spin-dried for, and then through pillar layer separation, (ladder is eluted, and is first eluted with petroleum ether, then use volume ratio
For ethyl acetate: petroleum ether=1:10) to obtain target compound.
It is characterized as below:
1,3- bis- (3,4- bromophenyl) acetone: yield: 60%, fusing point: 93-95 DEG C.1H NMR(500MHz,CDCl3)δ
7.49-7.45 (m, 2H), 7.43 (d, J=8.0Hz, 1H), 7.32 (s, 1H), 7.22 (t, J=7.8Hz, 1H), 7.10 (d, J=
7.6Hz, 1H), 7.04 (d, J=8.3Hz, 2H), 3.73 (s, 2H), 3.70 (s, 2H)
Embodiment 7
A 100mL round-bottomed flask is taken, by DCC (1.2371g, 6mmol), DMAP (0.2443g, 2mmol) and 4- bromobenzene
Acetic acid (0.7491g, 3.5mmol) is added in the dry methylene chloride of 12mL, stirs at 20 DEG C to whole dissolutions.By 3- bromobenzene
Acetic acid (0.7491g, 3.5mmol) is dissolved in the dry methylene chloride of 24mL, then with constant pressure funnel be slowly added dropwise to
In above-mentioned solution.Stirring for 24 hours, is spin-dried for, and then through pillar layer separation, (ladder is eluted, and is first eluted with petroleum ether, then be with volume ratio
Ethyl acetate: petroleum ether=1:10) to obtain target compound.
It is characterized as below:
1,3- bis- (3,4- bromophenyl) acetone: yield: 65%, fusing point: 93-95 DEG C.1H NMR(500MHz,CDCl3)δ
7.49-7.45 (m, 2H), 7.43 (d, J=8.0Hz, 1H), 7.32 (s, 1H), 7.22 (t, J=7.8Hz, 1H), 7.10 (d, J=
7.6Hz, 1H), 7.04 (d, J=8.3Hz, 2H), 3.73 (s, 2H), 3.70 (s, 2H)
Embodiment 8
A 250mL round-bottomed flask is taken, by DCC (2.0618g, 10mmol), DMAP (0.3665g, 3mmol) and 4- bromobenzene
Acetic acid (1.2842g, 6mmol) is added in the dry methylene chloride of 25mL, stirs at 20 DEG C to whole dissolutions.By 3- bromobenzene second
Sour (1.2842g, 6mmol) is dissolved in the dry methylene chloride of 50mL, is then slowly added dropwise with constant pressure funnel to above-mentioned
In solution.Stirring for 24 hours, is spin-dried for, and then through pillar layer separation, (ladder is eluted, and is first eluted with petroleum ether, then with volume ratio is acetic acid
Ethyl ester: petroleum ether=1:10) to obtain target compound.
It is characterized as below:
1,3- bis- (3,4- bromophenyl) acetone: yield: 66%, fusing point: 93-95 DEG C.1H NMR(500MHz,CDCl3)δ
7.49-7.45 (m, 2H), 7.43 (d, J=8.0Hz, 1H), 7.32 (s, 1H), 7.22 (t, J=7.8Hz, 1H), 7.10 (d, J=
7.6Hz, 1H), 7.04 (d, J=8.3Hz, 2H), 3.73 (s, 2H), 3.70 (s, 2H)
Embodiment 9
A 250mL round-bottomed flask is taken, by DCC (4.1236g, 20mmol), DMAP (0.7330g, 6mmol) and 4- bromobenzene
Acetic acid (2.5684g, 12mmol) is added in the dry methylene chloride of 30mL, stirs at 20 DEG C to whole dissolutions.By 3- bromobenzene
Acetic acid (2.5684g, 12mmol) is dissolved in the dry methylene chloride of 80mL, is then slowly added dropwise with constant pressure funnel supreme
It states in solution.Stirring for 24 hours, is spin-dried for, and then through pillar layer separation, (ladder is eluted, and is first eluted with petroleum ether, then with volume ratio is second
Acetoacetic ester: petroleum ether=1:10) to obtain target compound.
It is characterized as below:
1,3- bis- (3,4- bromophenyl) acetone: yield: 68%, fusing point: 93-95 DEG C.1H NMR(500MHz,CDCl3)δ
7.49-7.45 (m, 2H), 7.43 (d, J=8.0Hz, 1H), 7.32 (s, 1H), 7.22 (t, J=7.8Hz, 1H), 7.10 (d, J=
7.6Hz, 1H), 7.04 (d, J=8.3Hz, 2H), 3.73 (s, 2H), 3.70 (s, 2H)
In above 9 implementation cases column, case study on implementation 1 has obtained highest 1,3- bis- (3, the 4- bromophenyl) acetone of yield.
The preferable specific embodiment of the above, only the invention, but the protection scope of the invention is not
It is confined to this, anyone skilled in the art is in the technical scope that the invention discloses, according to the present invention
The technical solution of creation and its inventive concept are subject to equivalent substitution or change, should all cover the invention protection scope it
It is interior.
Claims (8)
1. one kind 1, the preparation method of 3- bis- (3,4- halogen phenyl) acetone, which is characterized in that the benzene second replaced with two kinds of halogens
Acid is raw material, and using DMAP as catalyst, DCC is dehydrating agent, is chemically reacted in organic solvent, finally obtains 1,3- bis-
(3,4- halogen phenyl) acetone；
The phenylacetic acid that two kinds of halogens replace is respectively halogen substitution between phenylacetic acid phenylacetic acid, halogen substitution；
What the halogen replaced is 1:1 to phenylacetic acid molar ratio between phenylacetic acid and halogen substitution；
The molar ratio to phenylacetic acid and DCC that the halogen replaces is 1~3:4~6, the halogen replace to phenylacetic acid
Molar ratio with DMAP is 2~4:1~2.
2. the preparation method of one kind 1,3- bis- (3,4- halogen phenyl) acetone as described in claim 1, which is characterized in that described
Organic solvent be dry methylene chloride；
The molar ratio to phenylacetic acid and dry methylene chloride that the halogen replaces is 1:40~80；
The molar ratio of phenylacetic acid and dry methylene chloride is 1:90~130 between the halogen replaces.
3. the preparation method of one kind 1,3- bis- (3,4- halogen phenyl) acetone as described in claim 1, which is characterized in that described
Halogen replace be to phenylacetic acid
Phenylacetic acid is between the halogen replaces
Wherein R3With R4For-Br.
4. the preparation method of one kind 1,3- bis- (3,4- halogen phenyl) acetone as claimed in claim 2, which is characterized in that preparation
Specific step is as follows for method:
S1. phenylacetic acid is added in round-bottomed flask by what DCC, DMAP and halogen replaced, and dry methylene chloride is added and stirs
It mixes uniformly；
S2. the isophthalic acetic acid that halogen replaces is slowly added dropwise into the reaction solution of step S1 in dichloromethane solution, 20
~30 DEG C of reaction 24-72h；
S3. it is filtered to remove the precipitating of step S2, obtains 1,3- bis- (3,4- halogen phenyl) third with column Chromatographic purification after filtrate revolving
Ketone.
5. the preparation method of one kind 1,3- bis- (3,4- halogen phenyl) acetone as claimed in claim 4, which is characterized in that described
Elution in step S3 column chromatography is that ladder elutes, and is first eluted with petroleum ether, then with volume ratio be ethyl acetate: petroleum ether=1:
10 elutions.
6. the preparation method of one kind 1,3- bis- (3,4- halogen phenyl) acetone as claimed in claim 4, which is characterized in that described
It is dry with anhydrous sodium sulfate before filtrate revolving in step 3.
7. the preparation method of one kind 1,3- bis- (3,4- halogen phenyl) acetone as claimed in claim 4, which is characterized in that described
The dropwise addition mode of step S2 is constant pressure funnel dropwise addition.
8. a kind of 1,3- bis- (3,4- halogen phenyl) acetone of preparation method preparation as described in claim 1 is in antidiabetic drug and light
The application of electrocrystallization conductor material preparation aspect.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108358767A (en) * | 2018-03-15 | 2018-08-03 | 吉林大学 | The double fluorine monomers of methylbenzene containing pentaphene, preparation method and its application in poly(aryl ether ketone) functional membrane |
| CN108752249A (en) * | 2018-04-25 | 2018-11-06 | 华南理工大学 | A kind of spatial conjugation organic molecule and its preparation and application based on six aryl benzene skeletons |
-
2019
- 2019-05-08 CN CN201910380452.XA patent/CN109942389A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108358767A (en) * | 2018-03-15 | 2018-08-03 | 吉林大学 | The double fluorine monomers of methylbenzene containing pentaphene, preparation method and its application in poly(aryl ether ketone) functional membrane |
| CN108752249A (en) * | 2018-04-25 | 2018-11-06 | 华南理工大学 | A kind of spatial conjugation organic molecule and its preparation and application based on six aryl benzene skeletons |
Non-Patent Citations (4)
| Title |
|---|
| BHANDARI, S.; RAY, S: "A Novel Synthesis of Bisbenzyl Ketones by DCC Induced Condensation of Phenylacetic Acid", 《SYNTH.COMMUN.》 * |
| SANDRA KURJATSCHIJ, WILHELM SEICHTER AND EDWIN WEBER: "Synthesis and structures of crystalline solvates formed of pyridinium N-phenoxide (Reichardt"s-type) betaine dyes and alcoholsw", 《NEW J. CHEM》 * |
| SUNIL VARUGHESE AND SYLVIA M. DRAPER: "Solid State Conformational Preferences of a Flexible Molecular Backbone Derived from Acetone: Dependence on Electron Donating/Withdrawing Ability of Substitutions", 《CRYSTAL GROWTH & DESIGN,》 * |
| YOSHIHIRO KIKUZAWA,TOMOHIKO MORI, AND HISATO TAKEUCHI: "Synthesis of 2,5,8,11,14,17-Hexafluoro-hexa perihexabenzocoronenefor n-Type Organic Field-Effect Transistors", 《ORGANIC LETTERS》 * |
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