CN112194685A - Preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride - Google Patents
Preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride Download PDFInfo
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- CN112194685A CN112194685A CN202011160419.5A CN202011160419A CN112194685A CN 112194685 A CN112194685 A CN 112194685A CN 202011160419 A CN202011160419 A CN 202011160419A CN 112194685 A CN112194685 A CN 112194685A
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- binaphthyl
- diphenylphosphino
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- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 title claims abstract description 62
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000001914 filtration Methods 0.000 claims abstract description 18
- 238000003756 stirring Methods 0.000 claims abstract description 18
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 16
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000005406 washing Methods 0.000 claims abstract description 11
- 239000012065 filter cake Substances 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 239000007787 solid Substances 0.000 claims abstract description 9
- 238000001291 vacuum drying Methods 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims description 5
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims description 5
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 238000000034 method Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 229910052751 metal Inorganic materials 0.000 abstract description 6
- 239000002184 metal Substances 0.000 abstract description 6
- 239000003446 ligand Substances 0.000 abstract description 3
- 239000002243 precursor Substances 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/006—Palladium compounds
- C07F15/0066—Palladium compounds without a metal-carbon linkage
Abstract
The invention discloses a preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride, which comprises the following steps: (1) under the protection of nitrogen, stirring and dissolving (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl at 30-50 ℃ by using an organic solvent; (2) dissolving a divalent palladium complex by using an organic solvent, then dropwise adding the divalent palladium complex into the solution obtained in the step (1), stirring and reacting for 5-10h at the temperature of 30-80 ℃, then heating and concentrating until solid is separated out, filtering, washing with water, filtering again, and carrying out vacuum drying on the obtained filter cake. The invention directly uses the complex of bivalent palladium as a metal precursor and [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] as a ligand, and has simple reaction process and high reaction yield.
Description
Technical Field
The invention belongs to the technical field of preparation of medical intermediates, and particularly relates to a preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride.
Background
The synthesis of chiral compounds is a scientific introduction of chemical synthesis at present, the chiral compounds are widely applied to the aspects of medicines, liquid crystal materials, functional materials, fine chemicals and the like, and chiral noble metal catalysts have great advantages in chiral synthesis due to the advantages of high reaction speed, high yield, high selectivity and the like in the aspect of chiral asymmetric synthesis.
The [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride plays an important role as a noble metal catalyst in specific organic synthesis reactions such as asymmetric hydrogenation, Heck, Suzuki reaction and the like.
The prior art adopts the direct coordination reaction of a ligand corresponding to a compound and a metal compound, so that the reaction yield is low, the metal unit consumption is high, and the purity of the obtained product is lower.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride, which directly uses a divalent palladium complex as a metal precursor, has high reaction yield, good quality and high metal utilization rate, and greatly reduces the reaction cost.
A preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride comprises the following steps:
(1) under the protection of nitrogen, stirring and dissolving (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl in an organic solvent at 30-50 ℃ to obtain an organic solution of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl;
(2) dissolving a divalent palladium complex by using an organic solvent, then dropwise adding the divalent palladium complex into the organic solution of the (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl, stirring and reacting for 5-10h at 30-80 ℃, then heating and concentrating until solid is separated out, filtering, washing with water, filtering again, and carrying out vacuum drying on the obtained filter cake.
Preferably, the divalent palladium complex is any one of (1, 5-cyclooctadiene) palladium (II) dichloride, (2, 2' -bipyridine) palladium (II) dichloride and bis (triphenylphosphine) palladium (II) dichloride.
Preferably, the organic solvent in step (1) and step (2) is the same, and the organic solvent is any one or two of tetrahydrofuran, dichloromethane, methanol, ethanol and toluene.
Preferably, in the step (1), the mass-to-volume ratio of the (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl to the organic solvent is 1 g: (3-10) mL; the mass-volume ratio of the divalent palladium complex to the organic solvent in the step (2) is 1 g: (3-10) mL; the molar ratio of the divalent palladium complex to (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl is 1: (1.05-1.2).
Preferably, the vacuum drying conditions are as follows: the temperature is 30-60 ℃, the time is 3-10h, and the vacuum degree is-0.08 to-0.095 Mpa.
Preferably, the water amount in the water washing is 3 to 10 times of the volume of the washed object.
The invention has the advantages that:
the invention directly utilizes the divalent palladium complex, comprises one of (1, 5-cyclooctadiene) palladium (II) dichloride, (2, 2' -bipyridine) palladium (II) dichloride and bis (triphenylphosphine) palladium (II) dichloride as a metal precursor, and [ (S) - (-) -2,2' -bis (diphenylphosphino) -1,1' -binaphthyl ] is used as a ligand, and the complex is directly heated for reaction, concentrated and filtered after being dissolved, so that the reaction process is simple, the reaction yield is high, the metal utilization rate is high, the product quality is good, and the reaction cost is greatly reduced.
Detailed Description
Example 1
A preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride comprises the following steps:
(1) under the protection of nitrogen, 11.45g of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl is dissolved by stirring at 30 ℃ by using 35mL of dichloromethane (AR) to obtain an organic solution of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl;
(2) dissolving 5.0g of (1, 5-cyclooctadiene) palladium (II) dichloride by using 15mL of dichloromethane (AR), then dropwise adding the solution into an organic solution of the (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl, stirring and reacting for 5h at 30 ℃, then heating and concentrating at 30 ℃ until solid is precipitated, filtering, washing with 3 times of volume of water, filtering again, and drying the obtained filter cake at 30 ℃ and under vacuum at-0.08 MPa for 10h to obtain 13.82g of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride;
in this example, the molar yield of the product, [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride, was 98.5%. The actual measurement element analysis result is as follows: c, 66.22; h, 0.04; cl: 8.82; p, 7.69; ru, 13.3; (theoretical elemental analysis result: C, 66; H, 0.04; Cl: 8.88; P, 7.74; Ru, 13.3).
Example 2
A preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride comprises the following steps:
(1) under the protection of nitrogen, 9.8g of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl is dissolved by stirring at 50 ℃ by using 29.4mL of toluene (AR) to obtain an organic solution of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl;
(2) dissolving 5.0g of (2, 2' -bipyridine) palladium (II) dichloride by using 15mL of toluene (AR), then dropwise adding the solution into an organic solution of the (S) - (-) -2,2' -bis (diphenylphosphino) -1,1' -binaphthyl, stirring and reacting for 10h at 80 ℃, then heating and concentrating at 30 ℃ until solid is precipitated, filtering, washing with 3 times of water by volume, filtering again, and drying the obtained filter cake at 60 ℃ and under vacuum at-0.095 MPa for 3h to obtain 11.77g of [ (S) - (-) -2,2' -bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride;
in this example, the molar yield of the product, [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride, was 98.1%. The actual measurement element analysis result is as follows: c, 66.1; h, 0.04; cl: 8.85; p, 7.71; ru, 13.3; (theoretical elemental analysis result: C, 66; H, 0.04; Cl: 8.88; P, 7.74; Ru, 13.3).
Example 3
A preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride comprises the following steps:
(1) under the protection of nitrogen, 4.66g of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl is dissolved by stirring at 50 ℃ by using 14mL of tetrahydrofuran (AR) to obtain an organic solution of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl;
(2) dissolving 5.0g of bis (triphenylphosphine) palladium (II) dichloride in 15mL of tetrahydrofuran (AR), dropwise adding the solution into an organic solution of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl, stirring and reacting for 8h at 50 ℃, heating and concentrating at 50 ℃ until solid is separated out, filtering, washing with 3 times of water, filtering again, and drying the obtained filter cake in vacuum at 30 ℃ and-0.095 MPa for 8h to obtain 5.6g of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride;
in this example, the molar yield of the product, [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride, was 98.3%. The actual measurement element analysis result is as follows: c, 66.11; h, 0.04; cl: 8.79; p, 7.72; ru, 13.32; (theoretical elemental analysis result: C, 66; H, 0.04; Cl: 8.88; P, 7.74; Ru, 13.3).
Example 4
A preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride comprises the following steps:
(1) under the protection of nitrogen, 13g of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl is dissolved by stirring at 40 ℃ by using 130mL of a mixed solution (AR) of methanol and ethanol to obtain an organic solution of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl;
(2) dissolving 5.0g of (1, 5-cyclooctadiene) palladium (II) dichloride by using 50mL of mixed solution (AR) of methanol and ethanol, then dropwise adding the solution into the organic solution of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl, stirring and reacting for 5h at 30 ℃, then heating and concentrating at 30 ℃ until solid is precipitated, filtering, washing with 10 times of water and filtering again, and drying the obtained filter cake at 30 ℃ and under vacuum at-0.095 MPa for 10h to obtain 13.72g of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride;
in this example, the product [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl]Moles of Palladium dichlorideYield is98% of the total weight of the composition. The actual measurement element analysis result is as follows: c, 66.12; h, 0.04; cl: 8.82; p, 7.69; ru, 13.31; (theoretical elemental analysis result: C, 66; H, 0.04; Cl: 8.88; P, 7.74; Ru, 13.3).
Example 5
A preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride comprises the following steps:
(1) under the protection of nitrogen, 11.2g of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl is dissolved by stirring at 50 ℃ by using 112mL of toluene (AR) to obtain an organic solution of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl;
(2) dissolving 5.0g of (2, 2' -bipyridine) palladium (II) dichloride with 50mL of toluene (AR), then dropwise adding the solution into the organic solution of (S) - (-) -2,2' -bis (diphenylphosphino) -1,1' -binaphthyl, stirring and reacting for 10h at 80 ℃, then heating and concentrating at 30 ℃ until solid is precipitated, filtering, washing with 10 times of water and filtering again, and drying the obtained filter cake at 60 ℃ and under vacuum at-0.095 MPa for 3h to obtain 7.35g of [ (S) - (-) -2,2' -bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride;
in this example, the molar yield of the product, [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride, was 98.1%. The actual measurement element analysis result is as follows: c, 66.05; h, 0.04; cl: 8.87; p, 7.69; ru, 13.3; (theoretical elemental analysis result: C, 66; H, 0.04; Cl: 8.88; P, 7.74; Ru, 13.3).
Example 6
A preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride comprises the following steps:
(1) under the protection of nitrogen, 5.32g of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl is dissolved at 50 ℃ by stirring using 53.2mL of tetrahydrofuran (AR) to obtain an organic solution of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl;
(2) dissolving 5.0g of bis (triphenylphosphine) palladium (II) dichloride in 50mL of tetrahydrofuran (AR), dropwise adding the solution into an organic solution of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl, stirring and reacting for 8 hours at 50 ℃, heating and concentrating at 80 ℃ until solid is separated out, filtering, washing with 10 times of water, filtering again, and drying the obtained filter cake at 30 ℃ and-0.08 MPa in vacuum for 8 hours to obtain 5.596g of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride;
in this example, the molar yield of the product, [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride, was 98.2%; the actual measurement element analysis result is as follows: c, 66.05; h, 0.04; cl: 8.87; p, 7.69; ru, 13.29; (theoretical elemental analysis result: C, 66; H, 0.04; Cl: 8.88; P, 7.74; Ru, 13.3).
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and all simple modifications, changes and equivalent structural changes made to the above embodiment according to the technical spirit of the present invention still fall within the protection scope of the technical solution of the present invention.
Claims (6)
1. A preparation method of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride is characterized in that: the method comprises the following steps:
(1) under the protection of nitrogen, stirring and dissolving (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl in an organic solvent at 30-50 ℃ to obtain an organic solution of (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl;
(2) dissolving a divalent palladium complex by using an organic solvent, then dropwise adding the divalent palladium complex into the organic solution of the (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl, stirring and reacting for 5-10h at 30-80 ℃, then heating and concentrating until solid is separated out, filtering, washing with water, filtering again, and carrying out vacuum drying on the obtained filter cake.
2. The process for preparing [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride according to claim 1, wherein: the divalent palladium complex is any one of (1, 5-cyclooctadiene) palladium (II) dichloride, (2, 2' -bipyridine) palladium (II) dichloride and bis (triphenylphosphine) palladium (II) dichloride.
3. The process for preparing [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride according to claim 2, wherein: the organic solvent in the step (1) and the organic solvent in the step (2) are the same, and the organic solvent is any one or two of tetrahydrofuran, dichloromethane, methanol, ethanol and toluene.
4. The process for preparing [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride according to claim 3, wherein: in the step (1), the mass-to-volume ratio of the (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl to the organic solvent is 1 g: (3-10) mL; the mass-volume ratio of the divalent palladium complex to the organic solvent in the step (2) is 1 g: (3-10) mL; the molar ratio of the divalent palladium complex to (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl is 1: (1.05-1.2).
5. The process for preparing [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride according to claim 4, wherein: the vacuum drying conditions are as follows: the temperature is 30-60 ℃, the time is 3-10h, and the vacuum degree is-0.08 to-0.095 Mpa.
6. The process for preparing [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1,1' -binaphthyl ] palladium dichloride according to claim 5, wherein: the water amount in the water washing is 3-10 times of the volume of the washed object.
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| CN114029092A (en) * | 2021-12-29 | 2022-02-11 | 苏利制药科技江阴有限公司 | Synthesis method of metal catalyst |
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