Difluoromethyl ether derivative and process for producing the same

A process for producing a difluoromethyl ether derivative represented by Formula (1c)

• wherein R1 and R2 each independently represent hydrogen, halogen, a cyano group or an alkyl group having 1 to 20 carbon atoms, in which at least one —CH2— may be substituted with —O—, —S—, —CH═CH— or —C≡C— but —O— is not adjacent to another —O—, and in which any hydrogen may be substituted with fluorine;
• rings A1, A2, A3 and A4 each independently represent a 1,4-cyclohexylene group in which at least one —CH2— may be substituted with —O— or —S—, or a 1,4-phenylene group in which at least one ═CH— may be substituted with ═N— and at least one hydrogen on the ring may be substituted with fluorine, a cyano group or an alkyl group having 1 to 10 carbon atoms;
• Z1, Z2, Z3 and Z4 each independently represent a single bond or an alkylene group having 1 to 4 carbon atoms, in which at least one —CH2— may be substituted with —O—, —S—, —CH═CH— or —C≡C— but —O— is not adjacent to another —O—, and in which any hydrogen may be substituted with fluorine;
• Y1, Y2, Y3 and Y4 each independently represent hydrogen, halogen, a cyano group or an alkyl group having 1 to 10 carbon atoms;
• and
• k, l, m and n each independently represent 0 or 1;
• which comprises:
• a first step of reacting the starting material, an α,α-difluorocyclohexylidene derivative represented by Formula (1a)
• wherein R1, rings A1 and A2, Z1, Z2, k and l have the same meanings as defined above;
• with halogen to produce a compound (1b)
• wherein R1, rings A1 and A2, Z1, Z2, k and l have the same meanings as defined above, and X represents chlorine, bromine or iodine;
• and
• a second step of reacting the compound (1b) with a phenol compound (P)
• wherein R2, rings A1 and A4, Z3, Z4, Y1, Y2, Y3, Y4, m and n have the same meanings as defined above;
• in the presence of a base to produce the compound (1c).