HU188368B - Process for preparing new 3-bromo-4-fluoro-benzaldehyde-acetal derivatives - Google Patents
Process for preparing new 3-bromo-4-fluoro-benzaldehyde-acetal derivatives Download PDFInfo
- Publication number
- HU188368B HU188368B HU803069A HU306980A HU188368B HU 188368 B HU188368 B HU 188368B HU 803069 A HU803069 A HU 803069A HU 306980 A HU306980 A HU 306980A HU 188368 B HU188368 B HU 188368B
- Authority
- HU
- Hungary
- Prior art keywords
- bromo
- fluorobenzaldehyde
- acetal derivatives
- benzaldehyde
- fluoro
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 9
- -1 3-Bromo-4-fluorobenzaldehyde Acetal Chemical class 0.000 claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- FAHZIKXYYRGSHF-UHFFFAOYSA-N 3-bromo-4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1Br FAHZIKXYYRGSHF-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OATOZCSPTSMOIY-UHFFFAOYSA-N 2-(3-bromo-4-fluorophenyl)-1,3-dioxolane Chemical compound C1=C(Br)C(F)=CC=C1C1OCCO1 OATOZCSPTSMOIY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- HNVVROFWONXXGO-UHFFFAOYSA-N (3-bromo-4-fluorophenyl)methanol Chemical compound OCC1=CC=C(F)C(Br)=C1 HNVVROFWONXXGO-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- BYQHKXISZJLWJG-UHFFFAOYSA-N 2-bromo-4-(dimethoxymethyl)-1-fluorobenzene Chemical compound COC(OC)C1=CC=C(F)C(Br)=C1 BYQHKXISZJLWJG-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QDKIFIYGNKHERN-UHFFFAOYSA-N 4-(bromomethyl)-1-fluoro-2-phenoxybenzene Chemical compound FC1=CC=C(CBr)C=C1OC1=CC=CC=C1 QDKIFIYGNKHERN-UHFFFAOYSA-N 0.000 description 1
- JDICMOLUAHZVDS-UHFFFAOYSA-N 4-fluoro-3-phenoxybenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1OC1=CC=CC=C1 JDICMOLUAHZVDS-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- BDUPRNVPXOHWIL-UHFFFAOYSA-N dimethyl sulfite Chemical compound COS(=O)OC BDUPRNVPXOHWIL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
- C07C45/305—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation with halogenochromate reagents, e.g. pyridinium chlorochromate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
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)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792933979 DE2933979A1 (de) | 1979-08-22 | 1979-08-22 | Neue 4-fluor-3-phenoxy-benzaldehydacetale und verfahren zu deren herstellung sowie neue zwischenprodukte hierfuer und verfahren zu deren herstellung. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU188368B true HU188368B (en) | 1986-04-28 |
Family
ID=6079042
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU803069A HU188368B (en) | 1979-08-22 | 1980-08-21 | Process for preparing new 3-bromo-4-fluoro-benzaldehyde-acetal derivatives |
| HU802071A HU185789B (en) | 1979-08-22 | 1980-08-21 | Process for preparing new 3-phenoxy-4-fluoro-benzaldehyde-acetal derivatives |
| HU803070A HU188369B (en) | 1979-08-22 | 1980-08-21 | Process for preparing 3-bromo-4-fluoro-benzaldehyde |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU802071A HU185789B (en) | 1979-08-22 | 1980-08-21 | Process for preparing new 3-phenoxy-4-fluoro-benzaldehyde-acetal derivatives |
| HU803070A HU188369B (en) | 1979-08-22 | 1980-08-21 | Process for preparing 3-bromo-4-fluoro-benzaldehyde |
Country Status (9)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2933985A1 (de) * | 1979-08-22 | 1981-04-09 | Bayer Ag, 5090 Leverkusen | Neue 4-fluor-3-phenoxy-benzyl-ether und verfahren zu deren herstellung sowie neue zwischenprodukte hierfuer und verfahren zu deren herstellung |
| DE3006685C2 (de) * | 1980-02-22 | 1982-09-09 | Riedel-De Haen Ag, 3016 Seelze | 3-Brom-4-fluorbenzonitril und Verfahren zur Herstellung eines substituierten 3-Brom-4-fluorbenzols |
| DE3035921A1 (de) * | 1980-09-24 | 1982-05-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 3-brom-4fluor-benzaldehyd-acetalen, neue zwischenprodukte hierfuer und verfahren zu deren herstellung |
| DE3036967A1 (de) * | 1980-10-01 | 1982-05-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 3-brom-4-fluor-benzylalkohol und neue zwischenprodukte hierfuer |
| DE3129651A1 (de) * | 1981-07-28 | 1983-02-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 3-brom-4-fluor-benzaldehyd |
| DE3136561A1 (de) * | 1981-09-15 | 1983-03-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von para-substituierten 3-brombenzaldehyden |
| JPS5939842A (ja) * | 1982-08-31 | 1984-03-05 | Mitsui Petrochem Ind Ltd | アセタ−ル類の製造方法 |
| US5212211A (en) * | 1990-11-19 | 1993-05-18 | Loctite Corporation | Polymodal-cure silicone composition, and method of making the same |
| US5182315A (en) * | 1990-11-19 | 1993-01-26 | Loctite Corporation | Photocurable silicone gel composition, and method of making the same |
| US5179134A (en) * | 1990-11-19 | 1993-01-12 | Loctite Corporation | Photocurable silicone composition, and method of making the same |
| FR2669925B1 (fr) * | 1990-11-30 | 1993-01-29 | Rhone Poulenc Chimie | Procede de preparation de composes aromatiques polyalkoxyles. |
| DE4106908A1 (de) * | 1991-03-05 | 1992-09-10 | Basf Ag | Verfahren zur herstellung (alpha),(beta)-ungesaettigter aldehyde und ketone |
| IL123137A0 (en) * | 1998-02-02 | 1998-09-24 | Bromine Compounds Ltd | Process for the halogenation of aldehydes and ketones |
| KR101586104B1 (ko) * | 2008-02-14 | 2016-01-15 | 스미또모 가가꾸 가부시끼가이샤 | 벤즈알데히드 화합물의 제조 방법 |
| JP5314330B2 (ja) * | 2008-06-16 | 2013-10-16 | 住友化学株式会社 | ２−（アリールオキシメチル）ベンズアルデヒドの製造方法およびその中間体 |
| WO2010086876A2 (en) * | 2009-01-09 | 2010-08-05 | Aditya Birla Science & Technology Co. Ltd. | Ether synthesis |
| TWI418535B (zh) * | 2009-04-07 | 2013-12-11 | Sumitomo Chemical Co | Preparation of benzaldehyde compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3904654A (en) * | 1973-08-06 | 1975-09-09 | Monsanto Co | Urea-phosphorus compounds |
| US3965127A (en) * | 1973-08-06 | 1976-06-22 | Monsanto Company | Urea-phosphorus compounds |
| FR2245630B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-10-02 | 1977-03-11 | Ile De France | |
| DE2934034A1 (de) * | 1979-08-22 | 1981-03-26 | Bayer Ag, 51373 Leverkusen | Verfahren zur herstellung von substituierten benzaldehyden, neue zwischenprodukte hierfuer und verfahren zu deren herstellung |
| DE3006685C2 (de) * | 1980-02-22 | 1982-09-09 | Riedel-De Haen Ag, 3016 Seelze | 3-Brom-4-fluorbenzonitril und Verfahren zur Herstellung eines substituierten 3-Brom-4-fluorbenzols |
| DE3026959A1 (de) * | 1980-07-16 | 1982-02-04 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 3-brom-4-fluor-benzaldehyd-(-acetalen) und neue zwischenprodukte hierfuer |
-
1979
- 1979-08-22 DE DE19792933979 patent/DE2933979A1/de not_active Withdrawn
-
1980
- 1980-08-12 EP EP80104747A patent/EP0024624B1/de not_active Expired
- 1980-08-12 EP EP82101333A patent/EP0061004A1/de active Pending
- 1980-08-12 DE DE8080104747T patent/DE3068432D1/de not_active Expired
- 1980-08-19 IL IL60874A patent/IL60874A/xx unknown
- 1980-08-19 IL IL60873A patent/IL60873A0/xx unknown
- 1980-08-20 DD DD80223413A patent/DD153823A5/de unknown
- 1980-08-20 JP JP11355080A patent/JPS5632427A/ja active Granted
- 1980-08-21 HU HU803069A patent/HU188368B/hu unknown
- 1980-08-21 DK DK359280A patent/DK359280A/da not_active Application Discontinuation
- 1980-08-21 HU HU802071A patent/HU185789B/hu unknown
- 1980-08-21 HU HU803070A patent/HU188369B/hu unknown
- 1980-08-21 BR BR8005293A patent/BR8005293A/pt not_active IP Right Cessation
-
1981
- 1981-09-18 US US06/303,657 patent/US4626601A/en not_active Expired - Lifetime
-
1986
- 1986-07-21 US US06/887,471 patent/US4748257A/en not_active Expired - Lifetime
-
1987
- 1987-11-02 JP JP62275930A patent/JPS63119434A/ja active Granted
- 1987-11-02 JP JP62275931A patent/JPS63119435A/ja active Granted
-
1988
- 1988-03-02 US US07/162,788 patent/US4845249A/en not_active Expired - Lifetime
-
1990
- 1990-12-11 DK DK293690A patent/DK163815C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5632427A (en) | 1981-04-01 |
| JPS64380B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-01-06 |
| DK293690D0 (da) | 1990-12-11 |
| DE3068432D1 (en) | 1984-08-09 |
| DK359280A (da) | 1981-02-23 |
| DK293690A (da) | 1990-12-11 |
| DK163815B (da) | 1992-04-06 |
| DE2933979A1 (de) | 1981-03-12 |
| JPS6338007B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-07-28 |
| US4626601A (en) | 1986-12-02 |
| US4748257A (en) | 1988-05-31 |
| EP0024624A2 (de) | 1981-03-11 |
| HU188369B (en) | 1986-04-28 |
| EP0024624A3 (en) | 1981-06-17 |
| JPH0255412B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-11-27 |
| EP0061004A1 (de) | 1982-09-29 |
| US4845249A (en) | 1989-07-04 |
| HU185789B (en) | 1985-03-28 |
| EP0024624B1 (de) | 1984-07-04 |
| IL60874A0 (en) | 1980-10-26 |
| DD153823A5 (de) | 1982-02-03 |
| JPS63119434A (ja) | 1988-05-24 |
| IL60874A (en) | 1985-08-30 |
| DK163815C (da) | 1992-09-07 |
| BR8005293A (pt) | 1981-03-04 |
| JPS63119435A (ja) | 1988-05-24 |
| IL60873A0 (en) | 1980-10-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |