Method for producing alpha-fluoroacrylic acid
AssigneeDaikin Industries, Ltd.
InventorsAkihiro Gotou, Yosuke Kishikawa, Naoyuki Hoshiya, Makoto Matsuura
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Abstract
An object of the present invention is to provide a novel method for producing an α-fluoroacrylic acid ester compound. This problem is solved by a method for producing a compound represented by formula (1), wherein R1 and R2 are identical or different, and each represents an alkyl group or the like; and R3 is an alkyl group or the like, the method comprising step A of reacting a compound represented by formula (2) with R3—OH (3) and carbon monoxide in the presence of palladium, a double bond-containing compound (α), a diphosphine compound (β), and a base, to obtain the compound represented by formula (1) above.
Claims8
A method for producing a compound represented by formula (1) or a salt thereof:
- wherein
- R1 and R2 are identical or different, and each represents an alkyl group, a fluoroalkyl group, an aryl group optionally having one or more substituents, a halogen atom, or a hydrogen atom;
- R3o is a hydrogen atom or R3;
- and
- R3 is an alkyl group, a fluoroalkyl group, or an aryl group optionally having one or more substituents,
- the method comprising step A of reacting a compound represented by formula (2):
- wherein the symbols in the formula are as defined above,
- with carbon monoxide and an alcohol represented by formula (3):
- R3—OH (3)
- wherein the symbol in the formula is as defined above,
- in the presence of
- palladium,
- a double bond-containing compound (α) represented by formula (α):
- wherein
- Rb1 is a hydrogen atom or a C1-6 alkyl group,
- Rb2 is a hydrogen atom or a C1-6 alkyl group,
- Yb1 is ═O or ═CH—Ryb1,
- Yb2 is —H, ═O or ═CH—Ryb2,
- Ryb1 is a hydrogen atom or a C6-14 aryl group,
- Ryb2 is a C6-14 aryl group,
- or
- Rb1 and Yb1, taken together with the adjacent carbon atom, may form an aromatic hydrocarbon ring,
- Lb is a bond, C1-3 alkanediyl optionally having one or more side chains, or —C(═O)—,
- or
- Ryb1 and Ryb2 may be linked to each other to form -Ly-, wherein Ly is linear
- C1-2 alkanediyl optionally having one or more side chains,
- wherein one of the side chains in Lb
- (1) may be linked to one of the side chains in Ly to form linear C1-2 hydrocarbon diyl, or
- (2) may be linked to Rb1 to form C3-4 alkanediyl,
- a diphosphine compound (β) having, on each phosphorus atom, at least one substituent selected from the group consisting of alkyl and cycloalkyl groups, and
- a base, with the proviso that, in the reaction, the palladium, taken together with the compound represented by formula (2), the double bond-containing compound (α), the diphosphine compound (β), or carbon monoxide, or with one or more of these, may form a palladium complex (A),
- to obtain the compound represented by formula (1) or a salt thereof.
Dependencies are inferred from the claim text.