HUP0302239A2 - Eljárás alkoholok fluormetilezésére, halogénező dekarboxilezés útján - Google Patents
Eljárás alkoholok fluormetilezésére, halogénező dekarboxilezés útjánInfo
- Publication number
- HUP0302239A2 HUP0302239A2 HU0302239A HUP0302239A HUP0302239A2 HU P0302239 A2 HUP0302239 A2 HU P0302239A2 HU 0302239 A HU0302239 A HU 0302239A HU P0302239 A HUP0302239 A HU P0302239A HU P0302239 A2 HUP0302239 A2 HU P0302239A2
- Authority
- HU
- Hungary
- Prior art keywords
- general formula
- alpha
- fluoromethylation
- hydrogen atom
- decarboxylation
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 238000006114 decarboxylation reaction Methods 0.000 title abstract 2
- 238000005799 fluoromethylation reaction Methods 0.000 title abstract 2
- 150000001298 alcohols Chemical class 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 150000001805 chlorine compounds Chemical class 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 239000012320 chlorinating reagent Substances 0.000 abstract 1
- -1 fluoride compound Chemical class 0.000 abstract 1
- 239000012025 fluorinating agent Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 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
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
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)
Abstract
A találmány tárgya eljárás alkohol fluormetilezésére halogéneződekarboxilezéssel. Az eljárás abból áll, hogy egy R1C(CX3)2OHáltalános képletű alkoholt egy X2CH2CO2R2 általános képletű alfa-halogén-észterrel reagáltatja alfa-alkoxi-észtert állítanak elő, aholR1 jelentése hidrogénatom vagy alkilcsoport, R2 jelentése hidrogénatomvagy alkilcsoport, X jelentése bármely előfordulásnál egymástólfüggetlenül hidrogénatom, klór-, bróm- vagy fluoratom és X2 jelentésebrómatom vagy klóratom. A kapott alfa-alkoxi-észtertelszappanosítással alfa-alkoxi-savvá alakítják, amelyet ólom-tetraacetáttal és egy klórozószerrel visszafolyató hűtő alatt forralvaR1C(CH3)2OCH2C1 általános képletű kloridvegyületet kapnak. Akloridvegyületet fluorozószerrel reagáltatva R1 C(CX3)2OCH2F általánosképletű fluoridvegyületté alakítják. Ó
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/587,417 US6271422B1 (en) | 2000-06-01 | 2000-06-01 | Method for fluoromethylation of alcohols via halogenative decarboxylation |
PCT/US2001/015516 WO2001094286A1 (en) | 2000-06-01 | 2001-05-14 | Method for fluoromethylation of alcohols via halogenative decarboxylation |
Publications (2)
Publication Number | Publication Date |
---|---|
HUP0302239A2 true HUP0302239A2 (hu) | 2003-10-28 |
HUP0302239A3 HUP0302239A3 (en) | 2006-03-28 |
Family
ID=24349720
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU0302239A HUP0302239A3 (en) | 2000-06-01 | 2001-05-14 | Method for fluoromethylation of alcohols via halogenative decarboxylation |
Country Status (29)
Country | Link |
---|---|
US (1) | US6271422B1 (hu) |
EP (1) | EP1286939B1 (hu) |
JP (1) | JP2004508293A (hu) |
KR (1) | KR100799895B1 (hu) |
CN (1) | CN1283606C (hu) |
AR (1) | AR028664A1 (hu) |
AT (1) | ATE317839T1 (hu) |
AU (2) | AU2001261565B2 (hu) |
BG (1) | BG107336A (hu) |
BR (1) | BR0110776A (hu) |
CA (1) | CA2410428A1 (hu) |
CZ (1) | CZ20023790A3 (hu) |
DE (1) | DE60117258T2 (hu) |
DK (1) | DK1286939T3 (hu) |
ES (1) | ES2258085T3 (hu) |
HK (1) | HK1054371B (hu) |
HU (1) | HUP0302239A3 (hu) |
IL (2) | IL152857A0 (hu) |
MX (1) | MXPA02011851A (hu) |
NO (1) | NO20025791L (hu) |
NZ (1) | NZ522502A (hu) |
PE (1) | PE20011339A1 (hu) |
PL (1) | PL364001A1 (hu) |
PT (1) | PT1286939E (hu) |
SK (1) | SK17512002A3 (hu) |
TW (1) | TWI222435B (hu) |
UY (1) | UY26738A1 (hu) |
WO (1) | WO2001094286A1 (hu) |
ZA (1) | ZA200208850B (hu) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7083580B2 (en) | 2001-04-06 | 2006-08-01 | Mattioli Engineering Ltd. | Method and apparatus for skin absorption enhancement and transdermal drug delivery |
WO2005023175A2 (en) * | 2003-09-10 | 2005-03-17 | Cristália Produtos Químicos Farmacêuticos Ltda. | Stable pharmaceutical composition of fluoroether compound for anesthetic use, method for stabilizing a fluoroether compound, use of stabilizer agent for precluding the degradation of a fluoroether compound |
MX2007005899A (es) * | 2004-11-17 | 2007-07-24 | Minrad Inc | Metodo para la preparacion de sevoflurano. |
CN103664584B (zh) * | 2013-12-23 | 2015-06-03 | 湖南方盛制药股份有限公司 | a-氟代丙酰乙酸酯的制备方法 |
CN104529721B (zh) * | 2015-01-16 | 2017-04-19 | 河北一品制药有限公司 | 一种七氟烷的工业化制备方法 |
CN107698430B (zh) * | 2017-11-01 | 2021-01-08 | 华东医药(西安)博华制药有限公司 | 一种七氟烷反应液的后处理方法 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL32586A (en) * | 1968-10-28 | 1973-11-28 | Baxter Laboratories Inc | 1,3-polyhalo-2-propyl methyl and halomethyl ethers and their preparation |
US3683092A (en) | 1970-07-31 | 1972-08-08 | Baxter Laboratories Inc | Method of anesthesia |
US4250334A (en) | 1979-12-26 | 1981-02-10 | Baxter Travenol Laboratories, Inc. | Method of synthesizing fluoromethylhexafluoroisopropyl ether |
US4314087A (en) | 1979-12-26 | 1982-02-02 | Baxter Travenol Laboratories, Inc. | Methods of synthesizing hexafluoroisopropanol from impure mixtures and synthesis of a fluoromethyl ether therefrom |
US4469898A (en) | 1979-12-26 | 1984-09-04 | Baxter Travenol Laboratories, Inc. | Method of synthesizing fluoromethylhexafluoroisopropyl ether |
JPS57209235A (en) * | 1981-06-18 | 1982-12-22 | Sumitomo Chem Co Ltd | Tetrahydronaphthalene derivative and its preparation |
US4847427A (en) | 1988-04-13 | 1989-07-11 | E. I. Du Pont De Nemours And Company | Process for preparing fluorocarbon polyethers |
US4874901A (en) * | 1988-05-06 | 1989-10-17 | Boc, Inc. | Process for the production of polyfluorinated ethers |
US4996371A (en) | 1990-01-16 | 1991-02-26 | Boc, Inc. | Method for fluorodecarboxylation |
JP3441735B2 (ja) * | 1996-02-21 | 2003-09-02 | セントラル硝子株式会社 | フルオロメチル−1,1,1,3,3,3−ヘキサフルオロイソプロピルエーテルの製造方法 |
US5789630A (en) | 1996-02-27 | 1998-08-04 | University Of Iowa Research Foundation | Process for the synthesis of hexafluoropropanes |
US5705710A (en) | 1997-01-15 | 1998-01-06 | University Of Iowa Research Foundation | Process for the synthesis of hexafluoroisopropyl ethers |
US5969193A (en) * | 1997-08-18 | 1999-10-19 | Medeva Pharmaceuticals Pa, Inc. | Method for the preparation of sevoflurane |
US5886239A (en) * | 1997-11-21 | 1999-03-23 | Baxter International Inc. | Method of preparing monofluoromethyl ethers |
US6100434A (en) * | 1999-03-26 | 2000-08-08 | Abbott Laboratories | Method for synthesizing sevoflurane and an intermediate thereof |
US6303831B1 (en) * | 2000-06-01 | 2001-10-16 | Abbott Laboratories | Synthetic method for fluoromethylation of halogenated alcohols |
US6245949B1 (en) * | 2000-06-01 | 2001-06-12 | Abbott Laboratories | Synthetic method for the fluoromethylation of alcohols |
-
2000
- 2000-06-01 US US09/587,417 patent/US6271422B1/en not_active Expired - Lifetime
-
2001
- 2001-05-14 WO PCT/US2001/015516 patent/WO2001094286A1/en active IP Right Grant
- 2001-05-14 PT PT01935471T patent/PT1286939E/pt unknown
- 2001-05-14 CZ CZ20023790A patent/CZ20023790A3/cs unknown
- 2001-05-14 DE DE60117258T patent/DE60117258T2/de not_active Expired - Fee Related
- 2001-05-14 AU AU2001261565A patent/AU2001261565B2/en not_active Ceased
- 2001-05-14 IL IL15285701A patent/IL152857A0/xx unknown
- 2001-05-14 AU AU6156501A patent/AU6156501A/xx active Pending
- 2001-05-14 DK DK01935471T patent/DK1286939T3/da active
- 2001-05-14 MX MXPA02011851A patent/MXPA02011851A/es active IP Right Grant
- 2001-05-14 BR BR0110776-3A patent/BR0110776A/pt not_active IP Right Cessation
- 2001-05-14 SK SK1751-2002A patent/SK17512002A3/sk unknown
- 2001-05-14 ES ES01935471T patent/ES2258085T3/es not_active Expired - Lifetime
- 2001-05-14 EP EP01935471A patent/EP1286939B1/en not_active Expired - Lifetime
- 2001-05-14 NZ NZ522502A patent/NZ522502A/en unknown
- 2001-05-14 PL PL01364001A patent/PL364001A1/xx not_active IP Right Cessation
- 2001-05-14 CA CA002410428A patent/CA2410428A1/en not_active Abandoned
- 2001-05-14 AT AT01935471T patent/ATE317839T1/de not_active IP Right Cessation
- 2001-05-14 CN CNB018104053A patent/CN1283606C/zh not_active Expired - Fee Related
- 2001-05-14 HU HU0302239A patent/HUP0302239A3/hu unknown
- 2001-05-14 KR KR1020027016188A patent/KR100799895B1/ko not_active IP Right Cessation
- 2001-05-14 JP JP2002501804A patent/JP2004508293A/ja not_active Ceased
- 2001-05-31 AR ARP010102630A patent/AR028664A1/es unknown
- 2001-05-31 UY UY26738A patent/UY26738A1/es not_active Application Discontinuation
- 2001-06-01 PE PE2001000507A patent/PE20011339A1/es not_active Application Discontinuation
- 2001-06-01 TW TW090113351A patent/TWI222435B/zh not_active IP Right Cessation
-
2002
- 2002-10-31 ZA ZA200208850A patent/ZA200208850B/en unknown
- 2002-11-14 IL IL152857A patent/IL152857A/en not_active IP Right Cessation
- 2002-11-28 BG BG107336A patent/BG107336A/bg unknown
- 2002-12-02 NO NO20025791A patent/NO20025791L/no not_active Application Discontinuation
-
2003
- 2003-07-10 HK HK03105010.2A patent/HK1054371B/zh not_active IP Right Cessation
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FD9A | Lapse of provisional protection due to non-payment of fees |