CN106810411A - A kind of method of acyl chlorides and 1,2- dichloroethanes reaction generation ester - Google Patents

A kind of method of acyl chlorides and 1,2- dichloroethanes reaction generation ester Download PDF

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CN106810411A
CN106810411A CN201510860315.8A CN201510860315A CN106810411A CN 106810411 A CN106810411 A CN 106810411A CN 201510860315 A CN201510860315 A CN 201510860315A CN 106810411 A CN106810411 A CN 106810411A
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acyl chlorides
carbonate
chloride
reaction
dichloroethanes
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CN106810411B (en
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高爽
任兰会
王连月
吕迎
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Dalian Institute of Chemical Physics of CAS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B41/00—Formation or introduction of functional groups containing oxygen
    • C07B41/12—Formation or introduction of functional groups containing oxygen of carboxylic acid ester groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

The invention discloses a kind of acyl chlorides and 1, the method of 2- dichloroethanes reaction generation ester, with acyl chlorides, 1,2- dichloroethanes, carbonate are reaction substrate, DMAP (DMAP) is catalyst, so that in air or atmosphere of inert gases, heating, stirring reaction obtain corresponding ester products.Preparation method of the invention is first reaction substrate using acyl chlorides, 1,2- dichloroethanes, carbonate, is found that carbonate is the source of the oxygen in product first, finds that the reaction is free radical mechanism first.

Description

A kind of method of acyl chlorides and 1,2- dichloroethanes reaction generation ester
Technical field
The present invention relates to a kind of acyl chlorides and the method for 1,2- dichloroethanes reaction generation ester, and in particular to a kind of method of acyl chlorides and 1,2- dichloroethanes reaction generation ester.
Background technology
Esterification is an important reaction in organic chemistry.Ester type compound is also widely used for the synthesis of various fine chemicals.Traditional esterification uses carboxylic acid derivates and alcohol as reaction substrate.This kind of reaction is used as classical reaction write-in organic chemistry textbooks, such as acyl chlorides and correspondent alcohol reaction generation ester, or ester and other alcohol reaction generation ester.So far, in the presence of carbonate and DMAP (DMAP), acyl chlorides and 1,2- dichloroethanes reaction generation ester have not been reported.
The content of the invention
The invention discloses a kind of acyl chlorides and 1, the method of 2- dichloroethanes reaction generation ester, with different acyl chlorides, 1,2- dichloroethanes, carbonate are reaction substrate, DMAP (DMAP) is catalyst, so that in air or atmosphere of inert gases, heating response obtains corresponding ester products.Preparation method of the invention is first reaction substrate using acyl chlorides, 1,2- dichloroethanes, carbonate, is found that carbonate is the source of the oxygen in product first, finds that the reaction is free radical mechanism first.
The technical scheme that the method for the invention is used for：
In air or atmosphere of inert gases, with acyl chlorides, 1,2- dichloroethanes, carbonate as reaction substrate, DMAP (DMAP) is catalyst, heating, stirring reaction, and product is post-treated to obtain described ester compounds.
Described carbonate is cesium carbonate, potassium carbonate, sodium carbonate, lithium carbonate.
The chemical formula of the acyl chlorides is RCOCl, replaces on R and is connected with a carbon beyond base or is not connected with methyl, and methyl is connected with the carbon atom on COCl, wherein, R is the phenyl containing substitution base, the furyl containing substitution base, the thienyl containing substitution base；The substitution base is H, C1-4Alkyl, C1-4Alkoxy, halogen, CF3。
Described acyl chlorides be chlorobenzoyl chloride, o-methyl-benzene formyl chloride, m-methyl benzoyl formyl chloride, to methyl benzoyl chloride, o-methoxy benzoyl chloride, anisoyl chloride, 4- n-propylbenzenes formyl chloride, o-chlorobenzoyl chloride, o-fluoro-benzoyl chloride, 3- fluorobenzoyl chlorides, 4- bromo-benzoyl chlorides, 4- trifluoromethyl benzoyl chlorides, 2- phenylacetyls chlorine, thiophene -2- acyl chlorides, furans -2- acyl chlorides.
Described inert gas is argon gas, nitrogen.
Acyl chlorides, 1,2- dichloroethanes, the mol ratio of carbonate are 1:2:0.25-1:7:1.
The consumption of DMAP (DMAP) is 2 with acyl chloride compound mol ratio:100~10:100.
Reaction temperature is 50-100 DEG C, and the reaction time is 12-48h.
The process step of the product is column chromatography, and eluant, eluent is ethyl acetate and n-hexane, and the volume ratio of ethyl acetate and n-hexane is 1:50-1:10.
Because such scheme is used, the present invention has following advantages compared with prior art：
1. present invention employs have no document report with different acyl chlorides, 1,2- dichloroethanes, carbonate reaction substrate, DMAP (DMAP) is catalyst, with air or atmosphere of inert gases, the method for preparing corresponding ester products.
2. present invention firstly discovers that carbonate is the source of the oxygen in product.
3. present invention firstly discovers that the reaction is free radical mechanism.
4. reaction yield reaches as high as 96%.
Specific embodiment
With reference to embodiment in detail the present invention is described in detail, but the scope of the invention is not limited to following embodiments.
The method of acyl chlorides and 1,2- dichloroethanes reaction generation ester：
The synthesis of 2- chloroethyl benzoic ethers
0.5mmol chlorobenzoyl chlorides, 0.2-0.4mmol Cs are sequentially added in the reaction tube of 35mL2CO3, 2mol%DMAP, 1.5-3.5mmol 1,2- dichloroethanes.After reaction system stirs 12-24h at 50-100 DEG C, column chromatography treatment (ethyl acetate/n-hexane=1:50-1:10).
The yield of 2- chloroethyl benzoic ethers is 88% (81.2mg).Yellow oil.1H NMR(400MHz,CDCl3)δppm:8.09-8.03 (m, 2H), 7.54 (dd, J=6.3,2.1Hz, 1H), 7.43 (t, J=7.8Hz, 2H), 4.55 (td, J=5.8,3.4Hz, 2H), 3.79 (td, J=5.9,3.3Hz, 2H)；13C NMR(101MHz,CDCl3)δppm:(d, J=5.4Hz), 166.13,133.25,129.71 128.45,64.46,41.71.HRMS (ESI) for C9H9ClO2,calcd:184.0291,found:184.0291.
Following corresponding esters compound synthesis method is identical with the synthetic method of 2- chloroethyl benzoic ethers.
2- chloroethyl 3- methyl benzoic acid esters
Yield 91% (90.4mg) brown oils；1H NMR(400MHz,CDCl3)δppm:7.87 (d, J=7.5Hz, 2H), 7.36 (dt, J=14.9,7.4Hz, 2H), 4.60-4.52 (m, 2H), 3.86-3.77 (m, 2H), 2.41 (s, 3H)；13C NMR(101MHz,CDCl3)δppm:166.39,138.28,134.06,130.26,129.55,128.36,126.91,64.41,41.70,21.28.HRMS(ESI)for C10H11ClO2,calcd:198.0448,found:198.0444.
2- chloroethyl 2- methyl benzoic acid esters
Yield 95% (94.3mg) yellow oils；1H NMR(400MHz,CDCl3)δppm:7.88 (dd, J=8.1,1.3Hz, 1H), 7.35-7.29 (m, 1H), 7.16 (t, J=6.9Hz, 2H), 4.48-4.42 (m, 2H), 3.74-3.68 (m, 2H), 2.53 (s, 3H)；13C NMR(101MHz,CDCl3)δppm: 166.03,139.43,131.28,130.73,129.78,127.92,124.75,63.25,40.75,20.78.HRMS(ESI)for C10H11ClO2,calcd:198.0448,found:198.0447.
2- chloroethyl 4- methyl benzoic acid esters
Yield 92% (91.4mg) yellow oils；1H NMR(400MHz,CDCl3)δppm:7.86 (d, J=8.2Hz, 2H), 7.15 (d, J=8.0Hz, 2H), 4.45 (t, J=5.7Hz, 2H), 3.71 (t, J=5.7Hz, 2H), 2.31 (s, 3H)；13C NMR(101MHz,CDCl3)δppm:165.18,142.96,128.73,128.12,125.86,63.25,40.71,20.64.HRMS(ESI)for C10H11ClO2,calcd:198.0448,found:198.0446.
2- chloroethyl O-Anisic Acid esters
Yield 90% (96.6mg) water white oils；1H NMR(400MHz,CDCl3)δppm:7.84 (dd, J=7.9,1.6Hz, 1H), 7.47 (td, J=8.4,1.7Hz, 1H), 6.98 (dd, J=7.8,6.0Hz, 2H), 4.53 (t, J=5.7Hz, 2H), 3.89 (s, 3H), 3.79 (t, J=5.7Hz, 2H)；13C NMR(101MHz,CDCl3)δppm:165.52,159.47,133.95,131.81,120.16,119.32,112.10,64.26,56.00,41.75.HRMS(ESI)for C10H11ClO3,calcd:214.0397,found:214.0399.
2- chloroethyl 4- methoxy benzoic acid esters
Yield 93% (99.7mg) water white oils；1H NMR(400MHz,CDCl3)δppm:8.07-7.94 (m, 2H), 6.93 (d, J=8.8Hz, 2H), 4.54 (t, J=5.7Hz, 2H), 3.86 (s, 3H), 3.83-3.77 (m, 2H)；13C NMR(101MHz,CDCl3)δppm:165.92,163.63,131.82,122.01,113.71,64.20,55.47,41.82.HRMS(ESI)for C10H11ClO3,calcd:214.0397,found:214.0398.
2- chloroethyl 4- propylbenzoic acid esters
Yield 85% (96.3mg) brown oils；1H NMR(400MHz,CDCl3)δppm:7.91 (d, J=8.2Hz, 2H), 7.22-7.09 (m, 2H), 4.57-4.38 (m, 2H), 3.82-3.63 (m, 2H), 2.62-2.45 (m, 2H), 1.59 (dd, J=15.0,7.5Hz, 2H), 0.87 (t, J=7.3Hz, 3H)；13C NMR(101MHz,CDCl3)δppm:166.29,148.71,129.80,128.60, 127.11,64.30,41.75,38.08,24.25,13.74.HRMS(ESI)for C12H15ClO2,calcd:226.0761,found:226.0772.
2- chloroethyl 2- chlorobenzoic acid esters
Yield 83% (91mg) brown oils；1H NMR(400MHz,CDCl3)δppm:7.89 (dd, J=7.8,1.3Hz, 1H), 7.54-7.39 (m, 2H), 7.37-7.28 (m, 1H), 4.73-4.51 (m, 2H), 3.91-3.74 (m, 2H)；13C NMR(101MHz,CDCl3)δppm:165.16,134.02,132.92,131.65,131.21,129.41,126.66,64.90,41.47.HRMS(ESI)for C9H8Cl2O2,calcd:217.9901,found:217.9900.
2- chloroethyl 3- fluorobenzoates
Yield 87% (88.1mg) yellow oils；1H NMR(400MHz,CDCl3)δppm:7.79 (d, J=7.8Hz, 1H), 7.67 (ddd, J=9.3,2.4,1.5Hz, 1H), 7.36 (td, J=8.0,5.6Hz, 1H), 7.25-7.16 (m, 1H), 4.54-4.47 (m, 2H), 3.79-3.70 (m, 2H)；13C NMR(101MHz,CDCl3)δppm:164.04 (d, J=3.1Hz), 162.76,160.30,129.10 (d,), J=7.8Hz 124.48 (d, J=3.1Hz), 119.46,119.25,115.74,115.51,63.75,40.52.HRMS (ESI) for C9H8ClFO2,calcd:202.0197,found:202.0197.
2- chloroethyl 2- fluorobenzoates
Yield 88% (89mg) water white oils；1H NMR(400MHz,CDCl3)δppm:7.97 (td, J=7.6,1.8Hz, 1H), 7.60-7.47 (m, 1H), 7.25-7.12 (m, 2H), 4.63-4.55 (m, 2H), 3.85-3.78 (m, 2H)；13C NMR(101MHz,CDCl3)δppm:(d, J=9.0Hz), 163.86,163.42,160.83,134.86 132.19,124.03 (d, J=4.0Hz), 117.19,116.97,64.68,41.46.HRMS (ESI) for C9H8ClFO2,calcd:202.0197,found:202.0196.
2- chloroethyl 4- bromo-benzoates
Yield 82% (108mg) water white oils；1H NMR(400MHz,CDCl3)δppm:7.93 (d, J=8.6Hz, 2H), 7.60 (d, J=8.6Hz, 2H), 4.61-4.51 (m, 2H), 3.88-3.74 (m, 2H)；13C NMR(101MHz,CDCl3)δppm:192.09,165.49,131.84,131.27, 128.49,64.68,41.60.HRMS(ESI)for C9H8BrClO2,calcd:261.9396,found:261.9398.
2- chloroethyls 4- (trifluoromethyl) benzoic ether
Yield 63% (79.6mg) yellow oils；1H NMR(400MHz,CDCl3)δppm:8.19 (d, J=8.2Hz, 2H), 7.73 (d, J=8.4Hz, 2H), 4.66-4.56 (m, 2H), 3.87-3.77 (m, 2H)；13C NMR(101MHz,CDCl3)δppm:(d, J=3.6Hz), 165.00,130.19 125.51 (d, J=3.7Hz), 64.93,41.53,29.71,14.14.HRMS (ESI) for C10H8ClF3O2,calcd:252.0165,found:252.0169.
2- chloroethyl 2- phenylacetic acid esters
Yield 79% (78.5mg) yellow oils；1H NMR(400MHz,CDCl3)δppm:7.35-7.22(m,5H),4.38-4.24(m,2H),3.75-3.50(m,4H)；13C NMR(101MHz,CDCl3)δppm:171.25,133.69,129.34,128.67,127.28,64.40,41.57,41.09.HRMS(ESI)for C10H11ClO2,calcd:198.0448,found:198.0446.
2- chloroethyl thienyl -2- carbonic esters
Yield 93% (88.6mg) yellow oils；1H NMR(400MHz,CDCl3)δppm:7.83 (dd, J=3.7,1.2Hz, 1H), 7.58 (dd, J=5.0,1.2Hz, 1H), 7.10 (dd, J=4.9,3.8Hz, 1H), 4.58-4.46 (m, 2H), 3.84-3.71 (m, 2H)；13C NMR(101MHz,CDCl3)δppm:161.77,133.98,132.97,127.89,64.50,41.54.HRMS(ESI)for C7H7ClO2S,calcd:189.9855,found:189.9856.
Phenyl (pyridine radicals -4- bases) ketone
Yield 96% (83.8mg) yellow oils；1H NMR(400MHz,CDCl3)δppm:7.60 (dd, J=1.6,0.7Hz, 1H), 7.23 (dd, J=3.5,0.7Hz, 1H), 6.52 (dd, J=3.5,1.7Hz, 1H), 4.57-4.52 (m, 2H), 3.80-3.75 (m, 2H)；13C NMR(101MHz,CDCl3)δppm:158.20,146.76,144.04,118.70,111.98,64.29,41.42.HRMS(ESI)for C7H7ClO3,calcd:174.0084,found:174.0081。

Claims (9)

1. a kind of method that acyl chlorides and the reaction of 1,2- dichloroethanes generate ester, it is characterised in that in air or inertia In atmosphere, with acyl chlorides, 1,2- dichloroethanes, carbonate as reaction substrate, DMAP (DMAP) it is catalyst, heating, stirring reaction, product is post-treated to obtain described ester compounds.
2. method according to claim 1, it is characterised in that described carbonate is cesium carbonate, carbonic acid Potassium, sodium carbonate, lithium carbonate.
3. method according to claim 1, it is characterised in that the chemical formula of the acyl chlorides is RCOCl, R It is connected with a carbon beyond upper substitution base or is not connected with methyl, methyl is connected with the carbon atom on COCl, its In, R is the phenyl containing substitution base, the furyl containing substitution base, the thienyl containing substitution base；The substitution base It is H, C1-4Alkyl, C1-4Alkoxy, halogen, CF3。
4. method according to claim 1, it is characterised in that described acyl chlorides is chlorobenzoyl chloride, adjacent first Base chlorobenzoyl chloride, m-methyl benzoyl formyl chloride, to methyl benzoyl chloride, o-methoxy benzoyl chloride, to methoxy Base chlorobenzoyl chloride, 4- n-propylbenzenes formyl chloride, o-chlorobenzoyl chloride, o-fluoro-benzoyl chloride, 3- fluorobenzoyls Chlorine, 4- bromo-benzoyl chlorides, 4- trifluoromethyl benzoyl chlorides, 2- phenylacetyls chlorine, thiophene -2- acyl chlorides, furans - 2- acyl chlorides.
5. method according to claim 1, it is characterised in that described inert gas is argon gas, nitrogen.
6. method according to claim 1, it is characterised in that acyl chlorides, 1,2- dichloroethanes, carbonate Mol ratio be 1:2:0.25-1:7:1.
7. method according to claim 2, it is characterised in that the use of DMAP (DMAP) Amount is 2 with acyl chloride compound mol ratio:100~10:100.
8. method according to claim 1, it is characterised in that reaction temperature is 50-100 DEG C, during reaction Between be 12-48h.
9. method according to claim 1, it is characterised in that the process step of the product is column chromatography, Eluant, eluent is ethyl acetate and n-hexane, and the volume ratio of ethyl acetate and n-hexane is 1:50-1:10.
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