USRE38325E1 - Method for the production of tetrakis (pentafluorophenyl) borates - Google Patents
Method for the production of tetrakis (pentafluorophenyl) borates Download PDFInfo
- Publication number
- USRE38325E1 USRE38325E1 US10/050,869 US5086902A USRE38325E US RE38325 E1 USRE38325 E1 US RE38325E1 US 5086902 A US5086902 A US 5086902A US RE38325 E USRE38325 E US RE38325E
- Authority
- US
- United States
- Prior art keywords
- pentafluorophenyl
- formula
- tetrakis
- compound
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 tetrakis (pentafluorophenyl) borates Chemical class 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title claims description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 claims abstract description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.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 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000002452 interceptive effect Effects 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- NIXOIRLDFIPNLJ-UHFFFAOYSA-M magnesium;benzene;bromide Chemical compound [Mg+2].[Br-].C1=CC=[C-]C=C1 NIXOIRLDFIPNLJ-UHFFFAOYSA-M 0.000 claims description 2
- 229910052700 potassium Chemical group 0.000 claims description 2
- 239000011591 potassium Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 4
- 150000004820 halides Chemical group 0.000 claims 2
- AMQDBUIQKQUCKY-UHFFFAOYSA-M magnesium;1,2,3,4,5-pentafluorobenzene-6-ide;bromide Chemical compound [Mg+2].[Br-].FC1=[C-]C(F)=C(F)C(F)=C1F AMQDBUIQKQUCKY-UHFFFAOYSA-M 0.000 claims 1
- 238000004293 19F NMR spectroscopy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- IGURZGCFZZUZSD-UHFFFAOYSA-N [Li]c1c(F)c(F)c(F)c(F)c1F Chemical compound [Li]c1c(F)c(F)c(F)c(F)c1F IGURZGCFZZUZSD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
Definitions
- This invention relates to the synthesis of tetrakis (pentafluorophenyl) borates by reaction of a tetrafluoroborate salt with a pentafluorophenyl compound.
- the invention provides a method for the production of tetrakis (pentafluorophenyl) borates by reacting a tetrafluoroborate salt with pentafluorophenyl magnesium halide in a non-interfering solvent.
- Pentafluorophenyl magnesium halides are known. See, e.g., Respess, et al., J. Organometal. Chem. (1969) 18:263-274 and Respess, et al., J. Organometal. Chem. (1969) 19:191-195.
- Pentafluorophenyl magnesium halides useful in the invention have the formula C 6 F 6 MgX in which X is a halogen, e.g., iodine, chlorine or bromine, preferably bromine.
- Tetrafluoroborate salts useful in the invention have the formula QBF 4 in which Q is sodium, lithium or potassium, preferably sodium.
- the reaction between the Grignard and the tetrafluoroborate salt may be conducted in any non-interfering solvent.
- Typical solvents have the formula R—O—R′ in which the R and R′ are the same or different aliphatic hydrocarbon groups having 2-10 carbon atoms. Ethyl ether is preferred.
- the reaction is appropriately conducted at a temperature of 0° C. to 100° C., preferably at 30° C. to 35° C.
- the tetrafluoroborate salt is added to the Grignard solution in stoichiometric amounts or in such greater or lesser amount as may be deemed appropriate. In the preferred practice of the invention the tetrafluoroborate salt is added in an amount more than 15% of stoichiometric. Preferably the reaction mixture is refluxed to expedite the reaction.
- a reaction vessel is changed with 0.25 mol of C 6 H 5 MgBr and 0.056 mol of NaBF 4 in an ethyl ether solvent.
- the reaction mixture is refluxed overnight under nitrogen.
- the reaction mixture was processed to recover 24.4 g of brown solids. Apparent yield 62.1%.
- Example I was repeated using NaBF 4 ground by pestle and mortar and a 36 hour reflux time. Yield: 62.2% of a product having a tetrakis (pentafluorophenyl) borate purity of about 60% as indicated by 19 F NMR.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/050,869 USRE38325E1 (en) | 1999-07-14 | 2002-01-18 | Method for the production of tetrakis (pentafluorophenyl) borates |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/353,156 US6096928A (en) | 1999-07-14 | 1999-07-14 | Method for the production of tetrakis (pentafluorophenyl) borates |
US10/050,869 USRE38325E1 (en) | 1999-07-14 | 2002-01-18 | Method for the production of tetrakis (pentafluorophenyl) borates |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/353,156 Reissue US6096928A (en) | 1999-07-14 | 1999-07-14 | Method for the production of tetrakis (pentafluorophenyl) borates |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE38325E1 true USRE38325E1 (en) | 2003-11-18 |
Family
ID=23387989
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/353,156 Ceased US6096928A (en) | 1999-07-14 | 1999-07-14 | Method for the production of tetrakis (pentafluorophenyl) borates |
US10/050,869 Expired - Lifetime USRE38325E1 (en) | 1999-07-14 | 2002-01-18 | Method for the production of tetrakis (pentafluorophenyl) borates |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/353,156 Ceased US6096928A (en) | 1999-07-14 | 1999-07-14 | Method for the production of tetrakis (pentafluorophenyl) borates |
Country Status (1)
Country | Link |
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US (2) | US6096928A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003051892A1 (en) * | 2001-12-13 | 2003-06-26 | Exxonmobil Chemical Patents Inc. | Partially fluorinated naphthyl-based borates |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5488169A (en) * | 1992-12-28 | 1996-01-30 | Tosoh Akzo Corporation | Method of producing tetrakis(pentafluorophenyl)borate derivatives using pentafluorophenylmagnesium derivatives |
US5600005A (en) * | 1992-06-23 | 1997-02-04 | Idemitsu Kosan Co., Ltd. | Process for producing tetrakisflorophenylborate |
-
1999
- 1999-07-14 US US09/353,156 patent/US6096928A/en not_active Ceased
-
2002
- 2002-01-18 US US10/050,869 patent/USRE38325E1/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5600005A (en) * | 1992-06-23 | 1997-02-04 | Idemitsu Kosan Co., Ltd. | Process for producing tetrakisflorophenylborate |
US5488169A (en) * | 1992-12-28 | 1996-01-30 | Tosoh Akzo Corporation | Method of producing tetrakis(pentafluorophenyl)borate derivatives using pentafluorophenylmagnesium derivatives |
Also Published As
Publication number | Publication date |
---|---|
US6096928A (en) | 2000-08-01 |
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Owner name: ANTARES CAPITAL LP, AS AGENT, ILLINOIS Free format text: SECURITY INTEREST;ASSIGNOR:BOULDER SCIENTIFIC COMPANY, LLC;REEL/FRAME:049619/0182 Effective date: 20190628 Owner name: BOULDER SCIENTIFIC COMPANY, LLC, VIRGINIA Free format text: CERTIFICATE OF CONVERSION FROM A DELAWARE OR NON-DELAWARE CORPORATION TO A DELAWARE LIMITED LIABILITY COMPANY PURSUANT TO SECTION 18-214 OF THE LIMITED LIABILITY COMPANY ACT;ASSIGNOR:BOULDER SCIENTIFIC COMPANY;REEL/FRAME:049624/0023 Effective date: 20190627 |