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1. (WO1998049128) PROCESS FOR PREPARING A (HETERO)AROMATIC OLEFIN
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/1998/049128 International Application No.: PCT/NL1998/000231
Publication Date: 05.11.1998 International Filing Date: 24.04.1998
Chapter 2 Demand Filed: 05.10.1998
IPC:
C07B 37/04 (2006.01) ,C07C 2/86 (2006.01) ,C07C 41/30 (2006.01) ,C07C 67/343 (2006.01) ,C07C 231/12 (2006.01) ,C07C 253/30 (2006.01) ,C07C 255/34 (2006.01) ,C07D 207/267 (2006.01) ,C07D 213/127 (2006.01) ,C07D 307/54 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
B
GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
37
Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
04
Substitution
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
2
Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
86
by condensation between a hydrocarbon and a non-hydrocarbon
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
41
Preparation of ethers; Preparation of compounds having groups, groups or groups
01
Preparation of ethers
18
by reactions not forming ether-oxygen bonds
30
by increasing the number of carbon atoms, e.g. by oligomerisation
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
67
Preparation of carboxylic acid esters
30
by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
333
by isomerisation; by change of size of the carbon skeleton
343
by increase in the number of carbon atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
231
Preparation of carboxylic acid amides
12
by reactions not involving the formation of carboxamide groups
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
253
Preparation of carboxylic acid nitriles
30
by reactions not involving the formation of cyano groups
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
255
Carboxylic acid nitriles
01
having cyano groups bound to acyclic carbon atoms
32
having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
34
with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
207
Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
02
with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
18
having one double bond between ring members or between a ring member and a non-ring member
22
with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
24
Oxygen or sulfur atoms
26
2-Pyrrolidones
263
with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
267
with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
213
Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
02
having three double bonds between ring members or between ring members and non-ring members
04
having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
06
containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
127
Preparation from compounds containing pyridine rings
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
307
Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
02
not condensed with other rings
34
having two or three double bonds between ring members or between ring members and non-ring members
38
with substituted hydrocarbon radicals attached to ring carbon atoms
54
Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Applicants:
DSM N.V. [NL/NL]; Het Overloon 1 NL-6411 TE Heerlen, NL (AL, AM, AT, AU, AZ, BA, BB, BE, BF, BG, BJ, BR, BY, CA, CF, CG, CH, CI, CM, CN, CU, CY, CZ, DE, DK, EE, ES, FI, FR, GA, GB, GE, GH, GM, GN, GR, HU, ID, IE, IL, IS, IT, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MC, MD, MG, MK, ML, MN, MR, MW, MX, NE, NL, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, SN, SZ, TD, TG, TJ, TM, TR, TT, UA, UG, UZ, VN, YU, ZW)
DE VRIES, Johannes, Gerardus [NL/NL]; NL (UsOnly)
STEPHAN, Massoud [LB/NL]; NL (UsOnly)
Inventors:
DE VRIES, Johannes, Gerardus; NL
STEPHAN, Massoud; NL
Agent:
JACOBS, Monique, Sophie, Nicole; Octrooibureau DSM P.O. Box 9 NL-6160 MA Geleen, NL
Priority Data:
100589825.04.1997NL
Title (EN) PROCESS FOR PREPARING A (HETERO)AROMATIC OLEFIN
(FR) PROCEDE DE PREPARATION D'UNE OLEFINE (HETERO)AROMATIQUE
Abstract:
(EN) The invention relates to a process for preparing a (hetero)aromatic olefin, in which an optionally substituted olefin is arylated in the presence of a metal (compound) containing a metal from any one of groups 8, 9 or 10 of the Periodic System, a compound being chosen as the arylating agent that has the formula (1): Ar-CO-YCOA where Ar stands for an optionally substituted (hetero)aromatic group; A stands for an optionally substituted (hetero)aromatic or aliphatic group, an optionally substituted alkoxy or aryloxy group or a bond with Ar; Y stands for an optionally substituted heteroatom, and the arylation is carried out in the presence of a halide. As the arylating agent use is preferably made of an aromatic carboxylic anhydride, for example benzoic anhydride. Suitable for use as the (metal) compound containing a metal from any one of groups 8, 9 or 10 of the Periodic System is a compound from the group comprising PdCl2, PdBr2, PdI2, Na2PdCl4, Na2PdCl6, Pd2(dibenzylidene acetone)3, (Ph3P)4Pd, (PhCN)2PdCl2, Pd(OAc)2 and PdSO4. Suitable for use as the halide is a compound from the group comprising halides of alkali metals, quaternary ammonium halides and quaternary phosphonium halides.
(FR) L'invention concerne un procédé permettant de préparer une oléfine (hétéro)aromatique, selon lequel on aryle une oléfine éventuellement substituée en présence d'un composé métallique contenant un métal appartenant au groupe 8, 9 ou 10 de la classification périodique. Le composé choisi comme agent d'arylation a pour formule (1): Ar-CO-YCOA, dans laquelle Ar représente un groupe (hétéro)aromatique éventuellement substitué; A représente un groupe (hétéro)aromatique ou aliphatique éventuellement substitué, un groupe alcoxy ou aryloxy éventuellement substitué ou une liaison avec Ar; et Y représente un hétéro-atome éventuellement substitué. L'arylation s'effectue en présence d'un halogénure. Comme agent d'arylation, on utilise de préférence un anhydride carboxylique aromatique, par exemple l'anhydride benzoïque. Le composé métallique contenant un métal du groupe 8, 9 ou 10 de la classification périodique appartient au groupe qui comprend PdCl2, PdBr2, PdI2, Na2PdCl4, Na2PdCl6, Pd2(acétone de dibenzylidène)3, (phényl3-P)4Pd, (phényl-CN)2PdCl2, Pd(OAc)2 et PdSO4. L'halogénure utilisé est un composé appartenant au groupe qui comprend les halogénures de métaux alcalins, les halogénures d'ammonium quaternaire et les halogénures de phosphonium quaternaire.
Designated States: AL, AU, BA, BB, BG, BR, CA, CN, CU, CZ, EE, GE, HU, ID, IL, IS, JP, KP, KR, LC, LK, LR, LT, LV, MG, MK, MN, MX, NO, NZ, PL, RO, SG, SI, SK, SL, TR, TT, UA, US, UZ, VN, YU
African Regional Intellectual Property Organization (ARIPO) (GH, GM, KE, LS, MW, SD, SZ, UG, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, ML, MR, NE, SN, TD, TG)
Publication Language: English (EN)
Filing Language: Dutch (NL)
Also published as:
AU1998070857