Process for the preparation of ring compounds
AssigneeMerck & Co., Inc.
InventorsDetlef Pauluth, Peer Kirsch, Peter Baeuerle, Oliver Deeg
Life of this patent
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Abstract
In a process for the preparation of ring compounds via a combinatorial synthesis, the reaction procedure is based on a Suzuki coupling, subsequent halo-demetallation and finally a further Suzuki coupling. The Suzuki couplings are each carried out with a boronic acid or a boronic acid ester. The reaction procedure uses provides novel ring compounds and uses novel synthesis units used for this purpose. The novel ring compounds are suitable for use as constituents in liquid-crystalline mixtures.
Claims13
A ring compound formula XIII:
- wherein
- m and n are each 1,
- Y is a group selected from formulae XIV to XVII
- wherein one or two CH groups in the aromatic ring systems may be replaced by N,
- X is a single bond, —CH2—CH2—, —CH═CH—, —C≡C— or
- L, independently of one another, are identical or different and are R, F, Br, I, OH, OR, SH, SR, CN, NO2, NO, CHO, COOH, COOR, CONH2, CONHR, CONR2, CF3, NH2, NHR or NR2,
- R is an alkyl, alkenyl or acyl group having from 1 to 12 carbon atoms or an aryl group having 6 carbon atoms, which is optionally substituted by an alkyl group having from 1 to 12 carbon atoms,
- a, b, c, d, e and f, independently of one another, are identical or different and are 0, 1 or 2, and the sum (a+b+c+d+e+f) is 3 to 8, and
- R1 and R2, independently of one another, are identical or different and are H, F, Cl, CN, NCS, 2-oxapropyl, 2- or 3-oxabutyl, 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl, 2-, 3-, 4-, 5-, 6- or 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl, a straight-chain or branched, optionally chiral, alkyl radical or alkoxy radical having from 1 to 12 carbon atoms or an alkenyl radical or alkynyl radical having from 2 to 8 carbon atoms.
A compound according to formula XVIII for XVIIIg:
- wherein
- L1 to L6 are each, independently of one another, R, F, Br, I, OH, OR, SH, SR, CN, NO2, NO, CHO, COON, COOR, CONH2, CONHR, CONR2, CF3, NH2, NHR or NR2;
- R1 is an alkyl, alkenyl or acyl group having from 1 to 12 carbon atoms or an aryl group having 6 carbon atoms, which is optionally substituted by an alkyl group having from 1 to 12 carbon atoms,
- R1 and R2, independently of one another, are identical or different and are H, F, Cl, CN, NCS, a straight-chain or branched, optionally chiral, alkyl radical or alkoxy radical having from 1 to 12 carbon atoms or an alkenyl radical or alkynyl radical having from 2 to 8 carbon atoms.
A compound of formula XVIII
- wherein
- m and n are each 1;
- L is in each case, independently of one another, F, CF3 or CH3;
- a, b, c, and d, independently of one another, are identical or different and are 0, 1 or 2, and the sum (a+b+c+d) is 3 to 8;
- and
- R1 and R2, independently of one another, are identical or different and are H, F, Cl, CN, NCS, a straight-chain or branched, optionally chiral, alkyl radical or alkoxy radical having from 1 to 12 carbon atoms or an alkenyl radical alkoxy radical having from 2 to 8 carbon atoms.
Dependencies are inferred from the claim text.