IL123990A - Process for the preparation of 3-bromoanizole from nitrobenzene - Google Patents
Process for the preparation of 3-bromoanizole from nitrobenzeneInfo
- Publication number
- IL123990A IL123990A IL12399098A IL12399098A IL123990A IL 123990 A IL123990 A IL 123990A IL 12399098 A IL12399098 A IL 12399098A IL 12399098 A IL12399098 A IL 12399098A IL 123990 A IL123990 A IL 123990A
- Authority
- IL
- Israel
- Prior art keywords
- process according
- bromonitrobenzene
- nitrobenzene
- methoxide
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 84
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 230000008569 process Effects 0.000 title claims abstract description 57
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- PLDWAJLZAAHOGG-UHFFFAOYSA-N 1-bromo-3-methoxybenzene Chemical compound COC1=CC=CC(Br)=C1 PLDWAJLZAAHOGG-UHFFFAOYSA-N 0.000 title claims abstract description 14
- FWIROFMBWVMWLB-UHFFFAOYSA-N 1-bromo-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Br)=C1 FWIROFMBWVMWLB-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 30
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 12
- 239000012429 reaction media Substances 0.000 claims abstract description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 69
- 238000006243 chemical reaction Methods 0.000 claims description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
- -1 alkali metal methoxide Chemical class 0.000 claims description 14
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 239000011630 iodine Substances 0.000 claims description 13
- 230000031709 bromination Effects 0.000 claims description 12
- 238000005893 bromination reaction Methods 0.000 claims description 12
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 11
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 238000005191 phase separation Methods 0.000 claims description 9
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 8
- 238000011065 in-situ storage Methods 0.000 claims description 8
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 8
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 8
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 238000007865 diluting Methods 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- LQNUZADURLCDLV-IDEBNGHGSA-N nitrobenzene Chemical group [O-][N+](=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 LQNUZADURLCDLV-IDEBNGHGSA-N 0.000 claims description 4
- IPILPUZVTYHGIL-UHFFFAOYSA-M tributyl(methyl)azanium;chloride Chemical group [Cl-].CCCC[N+](C)(CCCC)CCCC IPILPUZVTYHGIL-UHFFFAOYSA-M 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical group CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 150000003738 xylenes Chemical class 0.000 claims description 2
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 3
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 238000004817 gas chromatography Methods 0.000 description 22
- 238000004458 analytical method Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000009467 reduction Effects 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000004821 distillation Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 239000008241 heterogeneous mixture Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- ZJOZUCVPNIVCJN-UHFFFAOYSA-N (3-bromophenyl)-(3-bromophenyl)imino-oxidoazanium Chemical compound C=1C=CC(Br)=CC=1[N+]([O-])=NC1=CC=CC(Br)=C1 ZJOZUCVPNIVCJN-UHFFFAOYSA-N 0.000 description 1
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 description 1
- LPOQWSWPRAGSBK-UHFFFAOYSA-N 1,2-dibromo-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Br)=C1Br LPOQWSWPRAGSBK-UHFFFAOYSA-N 0.000 description 1
- ZDFBKZUDCQQKAC-UHFFFAOYSA-N 1-bromo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1 ZDFBKZUDCQQKAC-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 1
- WXSYEKOJUAYNJD-UHFFFAOYSA-N BrC=1C=C(C=CC1)OC.BrC=1C=C(C=CC1)OC Chemical compound BrC=1C=C(C=CC1)OC.BrC=1C=C(C=CC1)OC WXSYEKOJUAYNJD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004153 Potassium bromate Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VEVQNDVHZNOSHX-UHFFFAOYSA-N bis(3-bromophenyl)diazene Chemical compound BrC1=CC=CC(N=NC=2C=C(Br)C=CC=2)=C1 VEVQNDVHZNOSHX-UHFFFAOYSA-N 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 229960004380 tramadol Drugs 0.000 description 1
- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL12399098A IL123990A (en) | 1998-04-07 | 1998-04-07 | Process for the preparation of 3-bromoanizole from nitrobenzene |
| CNB998048674A CN1170798C (zh) | 1998-04-07 | 1999-03-22 | 制备3-溴苯甲醚和3-溴硝基苯的新方法 |
| AT99910649T ATE251105T1 (de) | 1998-04-07 | 1999-03-22 | Verfahren zur herstellung von 3-bromanisol und 3- bromnitrobenzol |
| AU29548/99A AU2954899A (en) | 1998-04-07 | 1999-03-22 | New processes for the preparation of 3-bromoanisole and 3-bromonitrobenzene |
| HU0102301A HUP0102301A3 (en) | 1998-04-07 | 1999-03-22 | Processes for preparation of 3-bromoanisole and 3-bromonitrobenzene |
| CZ20003663A CZ301094B6 (cs) | 1998-04-07 | 1999-03-22 | Zpusob prípravy 3-bromanisolu |
| PL99343348A PL194723B1 (pl) | 1998-04-07 | 1999-03-22 | Sposób wytwarzania 3-bromoanizolu |
| PCT/IL1999/000161 WO1999051561A1 (en) | 1998-04-07 | 1999-03-22 | New processes for the preparation of 3-bromoanisole and 3-bromonitrobenzene |
| DE69911757T DE69911757T2 (de) | 1998-04-07 | 1999-03-22 | Verfahren zur herstellung von 3-bromanisol und 3-bromnitrobenzol |
| EP99910649A EP1070038B1 (en) | 1998-04-07 | 1999-03-22 | New processes for the preparation of 3-bromoanisole and 3-bromonitrobenzene |
| US09/680,961 US6380440B1 (en) | 1998-04-07 | 2000-10-05 | Processes for the preparation of 3-bromoanisole and 3-bromonitrobenzene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL12399098A IL123990A (en) | 1998-04-07 | 1998-04-07 | Process for the preparation of 3-bromoanizole from nitrobenzene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL123990A true IL123990A (en) | 2002-03-10 |
Family
ID=11071403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12399098A IL123990A (en) | 1998-04-07 | 1998-04-07 | Process for the preparation of 3-bromoanizole from nitrobenzene |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6380440B1 (pl) |
| EP (1) | EP1070038B1 (pl) |
| CN (1) | CN1170798C (pl) |
| AT (1) | ATE251105T1 (pl) |
| AU (1) | AU2954899A (pl) |
| CZ (1) | CZ301094B6 (pl) |
| DE (1) | DE69911757T2 (pl) |
| HU (1) | HUP0102301A3 (pl) |
| IL (1) | IL123990A (pl) |
| PL (1) | PL194723B1 (pl) |
| WO (1) | WO1999051561A1 (pl) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5940418B2 (ja) * | 2012-09-14 | 2016-06-29 | マナック株式会社 | ３−ハロゲン化アニリンの製造方法 |
| AU2013202782B2 (en) | 2013-03-14 | 2015-05-14 | Gen-Probe Incorporated | Apparatus for indexing and agitating fluid containers |
| CN103864622A (zh) * | 2014-01-23 | 2014-06-18 | 安徽华润涂料有限公司 | 一种3,5-二溴硝基苯合成的生产工艺 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2607802A (en) * | 1951-03-28 | 1952-08-19 | Dow Chemical Co | Bromination of aromatic compounds |
| US4418228A (en) | 1982-04-22 | 1983-11-29 | Gulf Research & Development Company | Process for ring bromination of nitrobenzene |
| RU1817764C (ru) * | 1988-12-30 | 1993-05-23 | Московское научно-производственное объединение "НИОПИК" | Способ получени бромсодержащих ароматических или конденсированных N- или О-содержащих гетероциклических соединений |
-
1998
- 1998-04-07 IL IL12399098A patent/IL123990A/en not_active IP Right Cessation
-
1999
- 1999-03-22 AT AT99910649T patent/ATE251105T1/de not_active IP Right Cessation
- 1999-03-22 PL PL99343348A patent/PL194723B1/pl not_active IP Right Cessation
- 1999-03-22 WO PCT/IL1999/000161 patent/WO1999051561A1/en active IP Right Grant
- 1999-03-22 CN CNB998048674A patent/CN1170798C/zh not_active Expired - Fee Related
- 1999-03-22 HU HU0102301A patent/HUP0102301A3/hu unknown
- 1999-03-22 CZ CZ20003663A patent/CZ301094B6/cs not_active IP Right Cessation
- 1999-03-22 AU AU29548/99A patent/AU2954899A/en not_active Abandoned
- 1999-03-22 DE DE69911757T patent/DE69911757T2/de not_active Expired - Lifetime
- 1999-03-22 EP EP99910649A patent/EP1070038B1/en not_active Expired - Lifetime
-
2000
- 2000-10-05 US US09/680,961 patent/US6380440B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0102301A3 (en) | 2003-01-28 |
| EP1070038A1 (en) | 2001-01-24 |
| ATE251105T1 (de) | 2003-10-15 |
| DE69911757T2 (de) | 2004-08-05 |
| CN1296467A (zh) | 2001-05-23 |
| EP1070038B1 (en) | 2003-10-01 |
| PL194723B1 (pl) | 2007-06-29 |
| US6380440B1 (en) | 2002-04-30 |
| CZ20003663A3 (cs) | 2001-04-11 |
| PL343348A1 (en) | 2001-08-13 |
| HUP0102301A2 (hu) | 2001-12-28 |
| AU2954899A (en) | 1999-10-25 |
| CZ301094B6 (cs) | 2009-11-04 |
| WO1999051561A1 (en) | 1999-10-14 |
| DE69911757D1 (de) | 2003-11-06 |
| CN1170798C (zh) | 2004-10-13 |
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