CA1209159A - Preparation of biaryl compounds - Google Patents
Preparation of biaryl compoundsInfo
- Publication number
- CA1209159A CA1209159A CA000452610A CA452610A CA1209159A CA 1209159 A CA1209159 A CA 1209159A CA 000452610 A CA000452610 A CA 000452610A CA 452610 A CA452610 A CA 452610A CA 1209159 A CA1209159 A CA 1209159A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- alkyl
- arylamine
- propionitrile
- benzene
- 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
Links
- -1 biaryl compounds Chemical class 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 41
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 31
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 12
- 238000010168 coupling process Methods 0.000 claims abstract description 10
- 150000004820 halides Chemical class 0.000 claims abstract description 10
- 230000008878 coupling Effects 0.000 claims abstract description 9
- 238000005859 coupling reaction Methods 0.000 claims abstract description 9
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000010494 dissociation reaction Methods 0.000 claims abstract description 5
- 230000005593 dissociations Effects 0.000 claims abstract description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 84
- 238000000034 method Methods 0.000 claims description 31
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 239000010949 copper Substances 0.000 claims description 10
- 229910052802 copper Inorganic materials 0.000 claims description 10
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 10
- 238000006193 diazotization reaction Methods 0.000 claims description 6
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 5
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical group [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 5
- 229940045803 cuprous chloride Drugs 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 3
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 abstract description 2
- 229960002390 flurbiprofen Drugs 0.000 abstract description 2
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- SKRDXYBATCVEMS-UHFFFAOYSA-N isopropyl nitrite Chemical compound CC(C)ON=O SKRDXYBATCVEMS-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000005347 biaryls Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001717 carbocyclic compounds Chemical class 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/488,192 US4482502A (en) | 1983-04-25 | 1983-04-25 | Preparation of biaryl compounds |
| US488,192 | 1990-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1209159A true CA1209159A (en) | 1986-08-05 |
Family
ID=23938699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000452610A Expired CA1209159A (en) | 1983-04-25 | 1984-04-24 | Preparation of biaryl compounds |
Country Status (6)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4721790A (en) * | 1983-02-25 | 1988-01-26 | Ethyl Corporation | Nucleophilic substitution process for fluoronitroaralkyloxazoline |
| JPS6451636U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1987-09-18 | 1989-03-30 | ||
| JPH0535827U (ja) * | 1991-10-03 | 1993-05-14 | 旭 光本 | 蝋塗り集束線香 |
| JPH0623889U (ja) * | 1992-08-07 | 1994-03-29 | 株式会社新来島どっく | コンテナ船の倉口間甲板構造 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE428560B (sv) * | 1974-07-22 | 1983-07-11 | Merck & Co Inc | Forfarande for framstellning av 5-(2,4-difluorofenyl)salicylsyra. |
| US3992459A (en) * | 1975-05-01 | 1976-11-16 | Merck & Co., Inc. | Preparation of biphenyl compounds |
| US4216340A (en) * | 1979-05-02 | 1980-08-05 | Merck & Co., Inc. | Preparation of 5-(2,4-difluorophenyl)salicylic acid and derivatives |
| NL8006497A (nl) * | 1979-12-19 | 1981-07-16 | Upjohn Co | Werkwijze voor het bereiden van arylpropionzuren. |
| JPS5716830A (en) * | 1980-07-03 | 1982-01-28 | Sagami Chem Res Center | Preparation of biphenyl derivative |
| DE3216851A1 (de) * | 1981-05-18 | 1982-12-02 | The Upjohn Co., 49001 Kalamazoo, Mich. | Verfahren zur herstellung von substituierten biphenylverbindungen |
| US4370278A (en) * | 1981-11-02 | 1983-01-25 | Ethyl Corporation | Nucleophilic substitution process |
| DE3247215A1 (de) * | 1982-12-18 | 1984-06-20 | Riedel-De Haen Ag, 3016 Seelze | Fluorhaltige biphenylverbindung und verfahren zu ihrer herstellung |
-
1983
- 1983-04-25 US US06/488,192 patent/US4482502A/en not_active Expired - Lifetime
-
1984
- 1984-04-24 CA CA000452610A patent/CA1209159A/en not_active Expired
- 1984-04-25 AT AT84400837T patent/ATE36521T1/de not_active IP Right Cessation
- 1984-04-25 EP EP84400837A patent/EP0123629B1/en not_active Expired
- 1984-04-25 DE DE8484400837T patent/DE3473440D1/de not_active Expired
- 1984-04-25 JP JP59083618A patent/JPS6034920A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0123629A3 (en) | 1985-12-18 |
| EP0123629B1 (en) | 1988-08-17 |
| EP0123629A2 (en) | 1984-10-31 |
| US4482502A (en) | 1984-11-13 |
| DE3473440D1 (en) | 1988-09-22 |
| JPS6034920A (ja) | 1985-02-22 |
| JPS6215530B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-04-08 |
| ATE36521T1 (de) | 1988-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |