RU2012122246A - OBTAINING A NEW CLASS OF LIQUID CRYSTAL COMPOUNDS CONTAINING A FOUR-VOLUME FLUORINE-CONTAINING FRAME OF A BRIDGE TYPE - Google Patents

Abstract

1. Compounds of general formula wherein Alk is an alkyl substituent: CH, CH, CH, CHR are substituents selected from the group: aryl - phenyl, 4-CHCH, 3-CHCH, 2-CHCH, 4-ClCH, 4-FCH, 2- FCH, 4-CHOCCH, 3,4-di (CHO) CH, 4-i-PrCH, 4-i-BuCH, 2-t-BuCH, 4- (n-CH) CH, 2-naphthyl, mesityl; alkyl - methyl, n-butyl, X represents oxygen or sulfur, n = 0, 1 or 2, CHCF is a fragment: at n = 2 CH-CF, at n = 1 CH = CF, at n = 0 С≡С .2. The compounds according to claim 1, which are 4-hexoxy-4 '- [2,2,3,3-tetrafluoro-3- (methylthio) propyl] biphenyl; 4-hexoxy-4' - [2,2,3,3-tetrafluoro -3- (butylthio) propyl] biphenyl; 4-hexoxy-4 '- [2,2,3,3-tetrafluoro-3- (phenylthio) propyl] biphenyl; 4-hexoxy-4' - {2,2,3 , 3-tetrafluoro-3 - [(4-methylphenyl) thio] propyl} biphenyl; 4-Hexyoxy-4 '- [2,2,3,3-tetrafluoro-3- (2-naphthylthio) propyl] biphenyl; 4- Hexoxy-4 '- {2,2,3,3-tetrafluoro-3 - [(4-isopropylphenyl) thio] propyl} biphenyl; 4-Hexoxy-4' - [2,2,3,3-tetrafluoro-3- (mesitylthio) propyl] biphenyl; 4-hexoxy-4 '- {2,2,3,3-tetrafluoro-3 - [(4-methoxyphenyl) thio] propyl} biphenyl; 4-hexoxy-4' - {2,2 , 3,3-tetrafluoro-3 - [(4-fluorophenyl) thio] ropil} biphenyl; 4- (Hexoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (4-methylphenoxy) prop-1-en-1-yl] biphenyl; 4- (Hexoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (3-methylphenoxy) prop-1-en-1-yl] biphenyl; 4- (Hexoxy) -4' - [(1Z) - 2,3,3-trifluoro-3- (2-methylphenoxy) prop-1-en-1-yl] biphenyl; 4- (Hexoxy) -4 '- [(1Z) -2,3,3-trifluoro-3 - (4-isobutylphenoxy) prop-1-en-1-yl] biphenyl; 4- (hexoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (4-octylphenoxy) prop-1 en-1-yl] biphenyl; 4- (hexoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (2-fluorophenoxy) prop-1-en-1-yl] biphenyl; 4- (Hexoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (4-chlorophenoxy) prop-1-en-1-yl] biphenyl; 4- (Butoxy) -4'- [(1Z) -2,3,3-trifluoro-3- (4-isobutylphenoxy) prop-1-en-1-yl] biphenyl; 4- (Detsok i) -4 '- [(1Z) -2,3,3-trifluoro-3- (4-isobutylphenoxy) prop-1-en-1-yl] biphenyl; 4- (Pentadecoxy) -4' - [(1Z ) -2,3,3-trifluoro-3- (4-isobutylphenoxy) prop-1-en-1-yl] biphenyl. 3. The method of obtaining �

Claims (3)

1. Compounds of the general formula

wherein Alk is an alkyl substituent: C ₄ H ₉ , C ₆ H ₁₃ , C ₁₀ H ₂₁ , C ₁₅ H ₃₁ R ₁ represents substituents selected from the group: aryl - phenyl, 4-CH ₃ C ₆ H ₄ , 3-CH ₃ C ₆ H ₄ , 2-CH ₃ C ₆ H ₄ , 4-ClC ₆ H ₄ , 4-FC ₆ H ₄ , 2-FC ₆ H ₄ , 4-CH ₃ OS ₆ H ₄ , 3,4-di (CH ₃ O) C ₆ H ₃ , 4-i-PrC ₆ H ₄ , 4-i-BuC ₆ H ₄ , 2-t-BuC ₆ H ₄ , 4- (n-C ₈ H ₁₇ ) C ₆ H ₄ , 2-naphthyl, mesityl; alkyl - methyl, n-butyl, X represents oxygen or sulfur, n = 0, 1 or 2, CH _n CF _n is a fragment: at n = 2 CH ₂ -CF ₂ , at n = 1 CH = CF, at n = 0 С≡С. 2. The compounds according to claim 1, which are 4-hexoxy-4 '- [2,2,3,3-tetrafluoro-3- (methylthio) propyl] biphenyl; 4-hexoxy-4 '- [2,2,3,3-tetrafluoro-3- (butylthio) propyl] biphenyl; 4-hexoxy-4 '- [2,2,3,3-tetrafluoro-3- (phenylthio) propyl] biphenyl; 4-hexoxy-4 '- {2,2,3,3-tetrafluoro-3 - [(4-methylphenyl) thio] propyl} biphenyl; 4-hexoxy-4 '- [2,2,3,3-tetrafluoro-3- (2-naphthylthio) propyl] biphenyl; 4-hexoxy-4 '- {2,2,3,3-tetrafluoro-3 - [(4-isopropylphenyl) thio] propyl} biphenyl; 4-hexoxy-4 '- [2,2,3,3-tetrafluoro-3- (mesitylthio) propyl] biphenyl; 4-hexoxy-4 '- {2,2,3,3-tetrafluoro-3 - [(4-methoxyphenyl) thio] propyl} biphenyl; 4-hexoxy-4 '- {2,2,3,3-tetrafluoro-3 - [(4-fluorophenyl) thio] propyl} biphenyl; 4- (Hexyoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (4-methylphenoxy) prop-1-en-1-yl] biphenyl; 4- (Hexyoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (3-methylphenoxy) prop-1-en-1-yl] biphenyl; 4- (Hexyoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (2-methylphenoxy) prop-1-en-1-yl] biphenyl; 4- (Hexyoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (4-isobutylphenoxy) prop-1-en-1-yl] biphenyl; 4- (Hexoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (4-octylphenoxy) prop-1-en-1-yl] biphenyl; 4- (Hexoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (2-fluorophenoxy) prop-1-en-1-yl] biphenyl; 4- (Hexoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (4-chlorophenoxy) prop-1-en-1-yl] biphenyl; 4- (Butoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (4-isobutylphenoxy) prop-1-en-1-yl] biphenyl; 4- (Deoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (4-isobutylphenoxy) prop-1-en-1-yl] biphenyl; 4- (Pentadecoxy) -4 '- [(1Z) -2,3,3-trifluoro-3- (4-isobutylphenoxy) prop-1-en-1-yl] biphenyl. 3. A method for producing compounds of general formula (I), wherein a cross-coupling reaction of 1-bromo-4- (3-bromo-2,2,3,3-tetrafluoropropyl) benzene with 4-alkyloxyboric acids is carried out, where Alk is C ₄ H ₉ , C ₆ H ₁₃ , C ₁₀ H ₂₁ , C ₁₅ H ₃₁ for 4-6 hours, using 1,2-dimethoxyethane as solvent, an aqueous solution of an inorganic base (NaOH, KOH, K ₂ CO ₃ , Na ₂ CO ₃ , CsCO ₃ ) and a palladium catalyst (Pd (PPh ₃ ) ₄ , PdCl ₂ (dppb), Pd (dba) ₂ , PdCl ₂ (PPh ₃ ) ₂ , Pd (OAc) ₂ ), then the obtained intermediate products in one case are converted to an organolithium substrate by mpem-butyllithium in absolute THF at -100 ° C and add various disulfides, R ₁ represents a methyl, n-butyl, phenyl, 4-CH ₃ C ₆ H _4, 4-iPrC ₆ H _4, 2-naphthyl, symmetrical thiosulfonic S-esters in which R ₁ is 4-FC ₆ H ₄ , 4-CH ₃ OS ₆ H ₄ , mesityl, in another case, are reacted with various substituted phenols R ₁ OH at 80 ° C. in DMSO in the presence of inorganic bases in which X represents an oxygen atom, R ₁ represents 4-CH ₃ C ₆ H ₄ , 3-CH ₃ C ₆ H ₄ , 2-CH ₃ C ₆ H ₄ , 4-ClC ₆ H ₄ , 2 -FC ₆ H _4, 3,4- (CH ₃ O) ₂ C ₆ H _3, 4-iBuC ₆ H _4, 2-tBuC ₆ H _4, 4- (C ₈ H ₁₇₎ C ₆ H _4, then on uschestvlyayut hydrogen fluoride elimination reaction of 1.0 M solution of sodium hexamethyldisilazide in THF at -80 ° C for 1-3 hours, while X represents the oxygen atom, Alk represents C ₆ H _13, R ₁ is 4-CH ₃ C ₆ H ₄ , 3-CH ₃ C ₆ H ₄ , 2-CH ₃ C ₆ H ₄ , 2-FC ₆ H ₄ , 4-iBuC ₆ H ₄ , 2-iBuC ₆ H ₄ .