Method for producing halogenated acrylic acid derivative

A method for producing a halogenated acrylic acid ester compound, comprising:

• subjecting a compound of formula (1) having a boiling point of at most 500° C. to R3OH removal reaction in a vapor phase in the presence of a solid catalyst which is at least one solid catalyst selected from the group consisting of a metal catalyst and a metal oxide catalyst to produce an ethene compound of formula (2), wherein the R3OH removal reaction is conducted by flowing a vaporized compound of formula (1) through a catalyst layer which comprises the solid catalyst:
• wherein each of R1 and R2 is independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, an aryl group, an aryloxy group, an alkyl group having a substituent, a cycloalkyl group having a substituent, an alkoxy group having a substituent, an aryl group having a substituent, or an aryloxy group having a substituent, and each of R3, R4 and R5 is independently an alkyl group, a cycloalkyl group, an aryl group, an alkyl group having a substituent, a cycloalkyl group having a substituent, or an aryl group having a substituent;
• reacting the ethene compound of formula (2) and a compound of formula (3) in the presence of a basic compound and a phase transfer catalyst which is at least one selected from the group consisting of a tetrabutylammonium salt, a trioctylmethylammonium salt and a benzyldimethyloctadecylammonium salt to produce a cyclopropane compound of formula (4):
• CHXYZ (3)
• wherein each of X, Y and Z is independently a halogen atom, and R1, R2, R4 and R5 are each as defined in formula (1);
• and
• subjecting the cyclopropane compound of formula (4) to R4Y removal reaction by heating the cyclopropane compound of formula (4) in a liquid phase or in a vapor phase to produce a halogenated acrylic acid ester compound of formula (5):
• wherein R1, R2 and R5 are each as defined in formula (1), and X is as defined in formula (4).