CN102603811A - Synthetic method of [1,1'- bis-(diphenyl phosphine) ferrocene] palladium dichloride methylene dichloride complex - Google Patents
Synthetic method of [1,1'- bis-(diphenyl phosphine) ferrocene] palladium dichloride methylene dichloride complex Download PDFInfo
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- CN102603811A CN102603811A CN2012100410276A CN201210041027A CN102603811A CN 102603811 A CN102603811 A CN 102603811A CN 2012100410276 A CN2012100410276 A CN 2012100410276A CN 201210041027 A CN201210041027 A CN 201210041027A CN 102603811 A CN102603811 A CN 102603811A
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- ferrocene
- methylene dichloride
- diphenylphosphine
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- palladium chloride
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Abstract
The invention discloses a synthetic method of a [1,1'- bis-(diphenyl phosphine) ferrocene] palladium dichloride methylene dichloride complex. The synthetic method comprises the following steps of: dissolving sodium chloropalladite to absolute ethyl alcohol to obtain an ethanol solution of the sodium chloropalladite; dissolving 1,1'- bis-(diphenyl phosphine) ferrocene to methylene dichloride to obtain a methylene dichloride solution of the 1,1'- bis-(diphenyl phosphine) ferrocene; and dropwise adding the ethanol solution of the sodium chloropalladite to the methylene dichloride solution of the 1,1'- bis-(diphenyl phosphine) ferrocene for stirring, reacting and filtering to obtain orange red [1,1'- bis-(diphenyl phosphine) ferrocene] palladium dichloride methylene dichloride complex crystal. In the synthetic method, the methylene dichloride is directly used as a solvent, a target product of the solvent complex is obtained through one-step synthesis, the reaction process is simple, the synthetic cycle is short, the production cost is low, the operation is easy, the reaction condition is mild, the product is precipitated in a crystal form, the purity is larger than 99%, and the yield is larger than 90%.
Description
Technical field
The invention belongs to chemosynthesis technical field, be specifically related to the compound method of a kind of [1,1 '-two (diphenylphosphine) ferrocene] palladium chloride methylene dichloride complex compound.
Background technology
With the bidentate phosphine ligands be main various phosphine bridge transition dinuclear complexs because its structure is special, have novel catalytic perfomance, thereby cause investigator's very big interest, ferrocene has also received people's extensive concern with its specific molecule structure.1,1 '-two (diphenylphosphine) ferrocene (dppf) is the Novel Ligands that organic bidentate phosphine ligands is combined with ferrocene, has specific flexible back bone, can form various bimetals and multi-metal complex with another transition metal atoms.This type title complex is widely used in the reactions such as silicon hydrogen addition of catalytic hydrogenation, C-C coupling, ketone.
[1,1 '-two (diphenylphosphine) ferrocene] palladium chloride methylene dichloride complex compound (Pd (dppf) Cl
2CH
2Cl
2) be Pd (II) and the bimetal solvent complex that dppf forms, be used for catalyzed carbonylation, cross-couplings and suzuki reaction etc.At present, the compound method of solvent complex compounds is generally: earlier synthetic presoma is (like PdCl
2(dppf)), then through presoma at corresponding solvent (like CH
2Cl
2) in recrystallization obtain.The preparation process of this approach is more loaded down with trivial details, and production cost is higher.
Summary of the invention
Technical problem to be solved by this invention is the deficiency to above-mentioned prior art, and the compound method of a kind of [1,1 '-two (diphenylphosphine) ferrocene] palladium chloride methylene dichloride complex compound is provided.This method directly is solvent with the methylene dichloride, and one-step synthesis obtains title product [1,1 '-two (diphenylphosphine) ferrocene] the palladium chloride methylene dichloride complex compound of solvent complex thing, has saved presoma PdCl
2(dppf) building-up process, reaction process is simple, and synthesis cycle is short, and production cost is low, and is easy to operate, and reaction conditions is gentle, and product is separated out with crystalline form, and purity is greater than 99%, and yield is greater than 90%.
For solving the problems of the technologies described above, the technical scheme that the present invention adopts is: the compound method of a kind of [1,1 '-two (diphenylphosphine) ferrocene] palladium chloride methylene dichloride complex compound is characterized in that this method may further comprise the steps:
Step 1, sodium chloropalladite is dissolved in the absolute ethyl alcohol, obtains the ethanolic soln of sodium chloropalladite;
Step 2, with 1,1 '-two (diphenylphosphine) ferrocene is dissolved in the methylene dichloride, obtain 1,1 '-dichloromethane solution of two (diphenylphosphine) ferrocene;
Step 3, under agitation condition, the ethanolic soln of sodium chloropalladite described in the step 1 is dripped in described in the step 21; 1 '-dichloromethane solution of two (diphenylphosphine) ferrocene in; In temperature stirring reaction 1h～4h under 25 ℃～35 ℃ the condition; Reaction finishes the after-filtration reaction solution, obtains orange red [1,1 '-two (diphenylphosphine) ferrocene] palladium chloride methylene dichloride complex compound crystallization; Said sodium chloropalladite and 1,1 '-mol ratio of two (diphenylphosphine) ferrocene is 1: 1.1～1.2.
The compound method of above-mentioned [1,1 '-two (diphenylphosphine) ferrocene] palladium chloride methylene dichloride complex compound, the consumption of absolute ethyl alcohol described in the step 1 is that every gram sodium chloropalladite is with 10mL～20mL absolute ethyl alcohol.
The compound method of above-mentioned [1,1 '-two (diphenylphosphine) ferrocene] palladium chloride methylene dichloride complex compound, the consumption of methylene dichloride described in the step 2 be every gram 1,1 '-two (diphenylphosphine) ferrocene is with 5mL～10mL methylene dichloride.
The present invention compared with prior art has the following advantages:
1, the present invention directly is solvent with the methylene dichloride, and one-step synthesis obtains title product [1,1 '-two (diphenylphosphine) ferrocene] the palladium chloride methylene dichloride complex compound of solvent complex thing, has saved presoma PdCl
2(dppf) building-up process, reaction process is simple, and synthesis cycle is short, and production cost is low, and is easy to operate.
2, reaction conditions of the present invention is gentle, and product is separated out with crystalline form, and purity is greater than 99%, and yield is greater than 90%.
Below in conjunction with accompanying drawing and embodiment, technical scheme of the present invention is done further detailed description.
Description of drawings
Fig. 1 is dppf, PdCl
2(dppf) and the embodiment of the invention 1 synthetic [1,1 '-two (diphenylphosphine) ferrocene] palladium chloride methylene dichloride complex compound three's infrared spectrum.
Embodiment
Embodiment 1
Step 1, with 2.00 the gram sodium chloropalladites be dissolved in the 30mL absolute ethyl alcohol, obtain the ethanolic soln of sodium chloropalladite;
Step 2, with 4.15 grams 1,1 '-two (diphenylphosphine) ferrocene is dissolved in the 41mL methylene dichloride, obtain 1,1 '-dichloromethane solution of two (diphenylphosphine) ferrocene;
Step 3, under agitation condition, the ethanolic soln of sodium chloropalladite described in the step 1 is dripped in described in the step 21; 1 '-dichloromethane solution of two (diphenylphosphine) ferrocene in; Be stirring reaction 1h under 25 ℃ the condition in temperature, reaction finishes the after-filtration reaction solution, obtains 5.01 grams orange red [1; 1 '-two (diphenylphosphine) ferrocene] crystallization of palladium chloride methylene dichloride complex compound, yield 90.46%.
Present embodiment directly is solvent with the methylene dichloride, and one-step synthesis obtains title product [1,1 '-two (diphenylphosphine) ferrocene] the palladium chloride methylene dichloride complex compound of solvent complex thing, has saved presoma PdCl
2(dppf) building-up process, reaction process is simple, and synthesis cycle is short, and easy to operate, the synthetic product purity reaches 99.4%, and yield reaches 90.46%.
Fig. 1 is part dppf (1,1 '-two (diphenylphosphine) ferrocene), title complex PdCl
2(dppf) ([1,1 '-two (diphenylphosphino) ferrocene] palladium chloride) and present embodiment synthetic PdCl
2(dppf) CH
2Cl
2The infrared spectrum of (i.e. [1,1 '-two (diphenylphosphine) ferrocene] palladium chloride methylene dichloride complex compound), 1479cm among the figure
-1, 1165cm
-1And 745cm
-1Belong to the absorbed oscillation peak of phenyl ring, 1434cm
-1And 828cm
-1Belong to the substituent absorbed oscillation of cyclopentadienyl peak, with PdCl
2(dppf) compare, at 721cm
-1And 1269cm
-1Absorption peak appears in the place, belong to respectively the C-Cl absorption peak and because of with contiguous Cl strengthen-CH
2-wagging vibration absorption peak.
Embodiment 2
Step 1, with 2.00 the gram sodium chloropalladites be dissolved in the 40mL absolute ethyl alcohol, obtain the ethanolic soln of sodium chloropalladite;
Step 2, with 4.52 grams 1,1 '-two (diphenylphosphine) ferrocene is dissolved in the 45mL methylene dichloride, obtain 1,1 '-dichloromethane solution of two (diphenylphosphine) ferrocene;
Step 3, under agitation condition, the ethanolic soln of sodium chloropalladite described in the step 1 is dripped in described in the step 21; 1 '-dichloromethane solution of two (diphenylphosphine) ferrocene in; Be stirring reaction 1h under 25 ℃ the condition in temperature, reaction finishes the after-filtration reaction solution, obtains 5.02 grams orange red [1; 1 '-two (diphenylphosphine) ferrocene] crystallization of palladium chloride methylene dichloride complex compound, yield 90.64%.
Present embodiment directly is solvent with the methylene dichloride, and one-step synthesis obtains title product [1,1 '-two (diphenylphosphine) ferrocene] the palladium chloride methylene dichloride complex compound of solvent complex thing, has saved presoma PdCl
2(dppf) building-up process, reaction process is simple, and synthesis cycle is short, and easy to operate, the synthetic product purity reaches 99.8%, and yield reaches 90.64%.
Embodiment 3
Step 1, with 2.00 the gram sodium chloropalladites be dissolved in the 20mL absolute ethyl alcohol, obtain the ethanolic soln of sodium chloropalladite;
Step 2, with 4.15 grams 1,1 '-two (diphenylphosphine) ferrocene is dissolved in the 21mL methylene dichloride, obtain 1,1 '-dichloromethane solution of two (diphenylphosphine) ferrocene;
Step 3, under agitation condition, the ethanolic soln of sodium chloropalladite described in the step 1 is dripped in described in the step 21; 1 '-dichloromethane solution of two (diphenylphosphine) ferrocene in; Be stirring reaction 2h under 25 ℃ the condition in temperature, reaction finishes the after-filtration reaction solution, obtains 5.20 grams orange red [1; 1 '-two (diphenylphosphine) ferrocene] crystallization of palladium chloride methylene dichloride complex compound, yield 93.89%.
Present embodiment directly is solvent with the methylene dichloride, and one-step synthesis obtains title product [1,1 '-two (diphenylphosphine) ferrocene] the palladium chloride methylene dichloride complex compound of solvent complex thing, has saved presoma PdCl
2(dppf) building-up process, reaction process is simple, and synthesis cycle is short, and easy to operate, the synthetic product purity reaches 99.8%, and yield reaches 93.89%.
Embodiment 4
Step 1, with 2.00 the gram sodium chloropalladites be dissolved in the 30mL absolute ethyl alcohol, obtain the ethanolic soln of sodium chloropalladite;
Step 2, with 4.15 grams 1,1 '-two (diphenylphosphine) ferrocene is dissolved in the 41mL methylene dichloride, obtain 1,1 '-dichloromethane solution of two (diphenylphosphine) ferrocene;
Step 3, under agitation condition, the ethanolic soln of sodium chloropalladite described in the step 1 is dripped in described in the step 21; 1 '-dichloromethane solution of two (diphenylphosphine) ferrocene in; Be stirring reaction 1h under 35 ℃ the condition in temperature, reaction finishes the after-filtration reaction solution, obtains 5.32 grams orange red [1; 1 '-two (diphenylphosphine) ferrocene] crystallization of palladium chloride methylene dichloride complex compound, yield 96.05%.
Present embodiment directly is solvent with the methylene dichloride, and one-step synthesis obtains title product [1,1 '-two (diphenylphosphine) ferrocene] the palladium chloride methylene dichloride complex compound of solvent complex thing, has saved presoma PdCl
2(dppf) building-up process, reaction process is simple, and synthesis cycle is short, and easy to operate, the synthetic product purity reaches 99.1%, and yield reaches 96.05%.
Embodiment 5
Step 1, with 2.00 the gram sodium chloropalladites be dissolved in the 30mL absolute ethyl alcohol, obtain the ethanolic soln of sodium chloropalladite;
Step 2, with 4.15 grams 1,1 '-two (diphenylphosphine) ferrocene is dissolved in the 30mL methylene dichloride, obtain 1,1 '-dichloromethane solution of two (diphenylphosphine) ferrocene;
Step 3, under agitation condition, the ethanolic soln of sodium chloropalladite described in the step 1 is dripped in described in the step 21; 1 '-dichloromethane solution of two (diphenylphosphine) ferrocene in; Be stirring reaction 4h under 25 ℃ the condition in temperature, reaction finishes the after-filtration reaction solution, obtains 5.26 grams orange red [1; 1 '-two (diphenylphosphine) ferrocene] crystallization of palladium chloride methylene dichloride complex compound, yield 94.97%.
Present embodiment directly is solvent with the methylene dichloride, and one-step synthesis obtains title product [1,1 '-two (diphenylphosphine) ferrocene] the palladium chloride methylene dichloride complex compound of solvent complex thing, has saved presoma PdCl
2(dppf) building-up process, reaction process is simple, and synthesis cycle is short, and easy to operate, the synthetic product purity reaches 99.2%, and yield reaches 94.97%.
Embodiment 6
Step 1, with 20.00 the gram sodium chloropalladites be dissolved in the 300mL absolute ethyl alcohol, obtain the ethanolic soln of sodium chloropalladite;
Step 2, with 41.5 grams 1,1 '-two (diphenylphosphine) ferrocene is dissolved in the 415mL methylene dichloride, obtain 1,1 '-dichloromethane solution of two (diphenylphosphine) ferrocene;
Step 3, under agitation condition, the ethanolic soln of sodium chloropalladite described in the step 1 is dripped in described in the step 21; 1 '-dichloromethane solution of two (diphenylphosphine) ferrocene in; Be stirring reaction 4h under 35 ℃ the condition in temperature, reaction finishes the after-filtration reaction solution, obtains 53.14 grams orange red [1; 1 '-two (diphenylphosphine) ferrocene] crystallization of palladium chloride methylene dichloride complex compound, yield 95.95%.
Present embodiment directly is solvent with the methylene dichloride, and one-step synthesis obtains title product [1,1 '-two (diphenylphosphine) ferrocene] the palladium chloride methylene dichloride complex compound of solvent complex thing, has saved presoma PdCl
2(dppf) building-up process, reaction process is simple, and synthesis cycle is short, and easy to operate, the synthetic product purity reaches 99.2%, and yield reaches 95.95%.
The above; It only is preferred embodiment of the present invention; Be not that the present invention is done any restriction, every according to inventing technical spirit to any simple modification, change and equivalent structure variation that above embodiment did, all still belong in the protection domain of technical scheme of the present invention.
Claims (3)
1. the compound method of one kind [1 '-two (diphenylphosphine) ferrocene] palladium chloride methylene dichloride complex compound is characterized in that this method may further comprise the steps:
Step 1, sodium chloropalladite is dissolved in the absolute ethyl alcohol, obtains the ethanolic soln of sodium chloropalladite;
Step 2, with 1,1 '-two (diphenylphosphine) ferrocene is dissolved in the methylene dichloride, obtain 1,1 '-dichloromethane solution of two (diphenylphosphine) ferrocene;
Step 3, under agitation condition, the ethanolic soln of sodium chloropalladite described in the step 1 is dripped in described in the step 21; 1 '-dichloromethane solution of two (diphenylphosphine) ferrocene in; In temperature stirring reaction 1h～4h under 25 ℃～35 ℃ the condition; Reaction finishes the after-filtration reaction solution, obtains orange red [1,1 '-two (diphenylphosphine) ferrocene] palladium chloride methylene dichloride complex compound crystallization; Said sodium chloropalladite and 1,1 '-mol ratio of two (diphenylphosphine) ferrocene is 1: 1.1～1.2.
2. the compound method of [1,1 '-two (diphenylphosphine) ferrocene] according to claim 1 palladium chloride methylene dichloride complex compound is characterized in that the consumption of absolute ethyl alcohol described in the step 1 is that every gram sodium chloropalladite is with 10mL～20mL absolute ethyl alcohol.
3. according to claim 1 [1; 1 '-two (diphenylphosphine) ferrocene] compound method of palladium chloride methylene dichloride complex compound; It is characterized in that, the consumption of methylene dichloride described in the step 2 be every gram 1,1 '-two (diphenylphosphine) ferrocene is with 5mL～10mL methylene dichloride.
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Cited By (2)
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| CN110194781A (en) * | 2018-02-27 | 2019-09-03 | 上海奥普迪诗化学科技有限公司 | A kind of preparation method of bis- (diphenylphosphine) the ferrocene palladium chloride dichloromethane complex of 1,1`- |
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| CN102786552A (en) * | 2012-08-08 | 2012-11-21 | 陕西瑞科新材料股份有限公司 | Preparation method of [1,1'-di(diphenyl phosphino) ferrocene] palladium dichloride (dppfPdCl2) |
| CN110194781A (en) * | 2018-02-27 | 2019-09-03 | 上海奥普迪诗化学科技有限公司 | A kind of preparation method of bis- (diphenylphosphine) the ferrocene palladium chloride dichloromethane complex of 1,1`- |
| CN110194781B (en) * | 2018-02-27 | 2023-12-08 | 上海奥普迪诗化学科技有限公司 | Preparation method of 1,1' -bis (diphenylphosphine) ferrocene palladium dichloride dichloromethane complex |
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Address after: 710201 Xi'an Province Economic and Technological Development Zone, Jing Wei Jing Jing Road, West Road, No. 6, No. Patentee after: XI'AN CATALYST NEW MATERIALS CO., LTD. Address before: Weiyang road 710016 Shaanxi city of Xi'an province No. 96 Patentee before: Xi'An Catalyst Chemical Co., Ltd. |