Preparation of 2-alkyl-6-(het)aryl-difluoromethoxy-naphthalene, -tetralin and -decalin compounds, for liquid crystal display, involves converting naphthalene compound into carboxylic acid derivative and reaction with phenol compound

摘要

Preparation of 2-alkyl-6-(phenyl-, -pyridyl-, -pyridazinyl-, -pyrimidinyl- and -pyrazinyl)-difluoromethoxy-naphthalene, -5,6,7,8-tetrahydronaphthalene and -trans-decalin compounds (I) involves converting a 6-substituted-naphthalene, -tetralin or -decalin compound (II) into a carboxylic acid derivative by eliminating a halogen or keto group and introducing a C1 structure; and reacting this derivative with a phenol (III). Preparation of 2-alkyl-6-(phenyl-, -pyridyl-, -pyridazinyl-, -pyrimidinyl- and -pyrazinyl)-difluoromethoxy-naphthalene, -5,6,7,8-tetrahydronaphthalene and -trans-decalin compounds of formula (I) involves (a) converting a 6-substituted-naphthalene, -tetralin or -decalin compound of formula (II) into a carboxylic acid derivative by eliminating a halogen or keto group and introducing a C1 structure; and (b) reacting this derivative with a phenol of formula (III): R-(-A1-Z-)m-B-CF2O-A2-(A3)n-R' (I); R-(A1-Z-)mBX (II); HO-A2(-A3)n-R' (III); R = alkyl, in which one or more CH2 groups may be replaced by O, CF2, CH=CH, CH=CF, CF=CF, excluding peroxide structures O-O and formaldehyde acetals O-CH2-O; A1 = 1,4-cyclohexylene, 2,5-1,3-dioxanylene, 1,3-cyclobutylene or 2,6-spiro(3.3)heptanylene; A2, A3 = 1,4-phenylene, in which 1-4 H atoms may be replaced by F or 1 or 2 CH groups may be replaced by N; Z = a single bond, -CH2-CH2-, -CF2-CF2-, -CH=CH-, -CF=CF-, -CH=CF- or -CF=CH-; B = 2,6-di-substituted naphthalene, -5,6,7,8-tetrahydronaphthalene or -trans-decalin; R' = R, F, OCF3, OCF2H, CF3, Cl, SF5, CN, NCS; m, n = 0 or 1.