IL121066A - Process for the preparation of 5 - bromo - 2 - fluorobenzeneboronic acid - Google Patents
Process for the preparation of 5 - bromo - 2 - fluorobenzeneboronic acidInfo
- Publication number
- IL121066A IL121066A IL12106697A IL12106697A IL121066A IL 121066 A IL121066 A IL 121066A IL 12106697 A IL12106697 A IL 12106697A IL 12106697 A IL12106697 A IL 12106697A IL 121066 A IL121066 A IL 121066A
- Authority
- IL
- Israel
- Prior art keywords
- bromo
- lithium
- fluorophenyl
- acid
- fluorobenzeneboronate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 52
- IGBDPRKNAFOOGY-UHFFFAOYSA-N (5-bromo-2-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC(Br)=CC=C1F IGBDPRKNAFOOGY-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 229910052744 lithium Inorganic materials 0.000 claims description 38
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- CGMYPZZMSOSDEW-UHFFFAOYSA-N [Li]C1=CC(Br)=CC=C1F Chemical compound [Li]C1=CC(Br)=CC=C1F CGMYPZZMSOSDEW-UHFFFAOYSA-N 0.000 claims description 19
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- -1 lithium cyclic amide Chemical class 0.000 claims description 11
- 230000003301 hydrolyzing effect Effects 0.000 claims description 10
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 10
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical group COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 125000001033 ether group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 239000000575 pesticide Substances 0.000 abstract description 4
- 150000002148 esters Chemical class 0.000 abstract description 2
- 239000002728 pyrethroid Substances 0.000 abstract description 2
- MKHDDTWHDFVYDQ-UHFFFAOYSA-N 2,4-dibromo-1-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1Br MKHDDTWHDFVYDQ-UHFFFAOYSA-N 0.000 description 7
- YPTHSYKJDRMAJY-UHFFFAOYSA-N 5-bromo-2-fluorophenol Chemical compound OC1=CC(Br)=CC=C1F YPTHSYKJDRMAJY-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- ZGPYVJBTCRCSKR-UHFFFAOYSA-N 4-bromo-2-(5-bromo-2-fluorophenoxy)-1-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1OC1=CC(Br)=CC=C1F ZGPYVJBTCRCSKR-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 3
- 229910001623 magnesium bromide Inorganic materials 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- RNTGKISRXVFIIP-UHFFFAOYSA-N 1,2-dibromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C(Br)=C1 RNTGKISRXVFIIP-UHFFFAOYSA-N 0.000 description 2
- GREWZYRZMVYLBQ-UHFFFAOYSA-N 4-bromo-1-fluoro-2-phenoxybenzene Chemical compound FC1=CC=C(Br)C=C1OC1=CC=CC=C1 GREWZYRZMVYLBQ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000005103 alkyl silyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- JCIVHYBIFRUGKO-UHFFFAOYSA-N lithium;2,2,6,6-tetramethylpiperidine Chemical compound [Li].CC1(C)CCCC(C)(C)N1 JCIVHYBIFRUGKO-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 1
- IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical compound FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- XGBBCUALFPDZIK-UHFFFAOYSA-N OBO.FC1=CC=C(Br)C=C1 Chemical compound OBO.FC1=CC=C(Br)C=C1 XGBBCUALFPDZIK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000010961 commercial manufacture process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- ZLRWTBOIOQQDBJ-UHFFFAOYSA-N lithium;benzylazanide Chemical compound [Li+].[NH-]CC1=CC=CC=C1 ZLRWTBOIOQQDBJ-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- UPRXAOPZPSAYHF-UHFFFAOYSA-N lithium;cyclohexyl(propan-2-yl)azanide Chemical compound CC(C)N([Li])C1CCCCC1 UPRXAOPZPSAYHF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
-
- 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
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL12910997A IL129109A (en) | 1996-06-14 | 1997-06-12 | Process for the preparation of fluoroolefin compounds |
| IL12910999A IL129109A0 (en) | 1996-06-14 | 1999-03-22 | A process for the preparation of fluoroolefin compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66375596A | 1996-06-14 | 1996-06-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL121066A0 IL121066A0 (en) | 1997-11-20 |
| IL121066A true IL121066A (en) | 2004-03-28 |
Family
ID=24663147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12106697A IL121066A (en) | 1996-06-14 | 1997-06-12 | Process for the preparation of 5 - bromo - 2 - fluorobenzeneboronic acid |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0812847B1 (da) |
| JP (1) | JPH1059980A (da) |
| KR (1) | KR100514980B1 (da) |
| CN (2) | CN1244531C (da) |
| AT (1) | ATE224901T1 (da) |
| BR (1) | BR9703531A (da) |
| DE (1) | DE69715733T2 (da) |
| DK (1) | DK0812847T3 (da) |
| ES (1) | ES2184033T3 (da) |
| IL (1) | IL121066A (da) |
| PL (1) | PL185310B1 (da) |
| TW (1) | TW369520B (da) |
| ZA (1) | ZA975173B (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2415193A (en) * | 2004-06-19 | 2005-12-21 | F2 Chemicals Ltd | Fluorinated arylboronic acids |
| JP5187025B2 (ja) * | 2008-06-26 | 2013-04-24 | Ｄｉｃ株式会社 | フルオロナフトール誘導体の製造方法 |
| KR101279240B1 (ko) | 2008-12-25 | 2013-06-26 | 닛뽕소다 가부시키가이샤 | 유기 리튬 화합물의 제조방법 및 치환 방향족 화합물의 제조방법 |
| WO2012114347A1 (en) * | 2011-02-21 | 2012-08-30 | Avra Laboratories Pvt. Ltd. | Synthesis of chiral substituted benzenes and related aromatic compounds containing 1,2 diols protected as diacetal groups |
| JP2012232924A (ja) * | 2011-04-28 | 2012-11-29 | Tosoh Corp | 新規なナフチルボロン酸化合物及びその製造法 |
| CN103570753A (zh) * | 2013-11-13 | 2014-02-12 | 大连九信生物化工科技有限公司 | 一种芳基硼酸化合物的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2579310B2 (ja) * | 1986-03-13 | 1997-02-05 | ブリティッシュ・テクノロジー・グループ・リミテッド | 殺虫剤製造用中間体 |
| GB2226315B (en) * | 1986-03-13 | 1991-02-06 | Nat Res Dev | Intermediates useful in the production of pesticides |
| DE59108963D1 (de) * | 1990-02-01 | 1998-05-20 | Merck Patent Gmbh | Verfahren zur Umsetzung von fluorierten Aromaten mit Elektrophilen |
-
1997
- 1997-05-27 TW TW086107146A patent/TW369520B/zh active
- 1997-06-11 BR BR9703531A patent/BR9703531A/pt not_active Application Discontinuation
- 1997-06-11 KR KR1019970023991A patent/KR100514980B1/ko not_active IP Right Cessation
- 1997-06-11 ZA ZA975173A patent/ZA975173B/xx unknown
- 1997-06-12 JP JP9169671A patent/JPH1059980A/ja not_active Ceased
- 1997-06-12 DK DK97304114T patent/DK0812847T3/da active
- 1997-06-12 EP EP97304114A patent/EP0812847B1/en not_active Expired - Lifetime
- 1997-06-12 IL IL12106697A patent/IL121066A/en not_active IP Right Cessation
- 1997-06-12 ES ES97304114T patent/ES2184033T3/es not_active Expired - Lifetime
- 1997-06-12 DE DE69715733T patent/DE69715733T2/de not_active Expired - Fee Related
- 1997-06-12 AT AT97304114T patent/ATE224901T1/de not_active IP Right Cessation
- 1997-06-13 PL PL97320554A patent/PL185310B1/pl not_active IP Right Cessation
- 1997-06-13 CN CNB011377569A patent/CN1244531C/zh not_active Expired - Fee Related
- 1997-06-13 CN CN97112744A patent/CN1087743C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1403430A (zh) | 2003-03-19 |
| DE69715733T2 (de) | 2003-05-22 |
| BR9703531A (pt) | 1998-10-06 |
| ATE224901T1 (de) | 2002-10-15 |
| CN1244531C (zh) | 2006-03-08 |
| DK0812847T3 (da) | 2002-10-14 |
| ZA975173B (en) | 1998-12-11 |
| EP0812847A1 (en) | 1997-12-17 |
| IL121066A0 (en) | 1997-11-20 |
| ES2184033T3 (es) | 2003-04-01 |
| DE69715733D1 (de) | 2002-10-31 |
| CN1087743C (zh) | 2002-07-17 |
| CN1168887A (zh) | 1997-12-31 |
| PL320554A1 (en) | 1997-12-22 |
| PL185310B1 (pl) | 2003-04-30 |
| JPH1059980A (ja) | 1998-03-03 |
| EP0812847B1 (en) | 2002-09-25 |
| TW369520B (en) | 1999-09-11 |
| KR100514980B1 (ko) | 2006-01-27 |
| KR980002054A (ko) | 1998-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |