Fluorine-containing aromatic compound and production method thereof
View Patent ↗A method of manufacturing a fluorine-containing aromatic compound represented by the following formula (2-1) or formula (2-2): R 1 is a linear perfluoroalkyl group having a carbon number of 1 to 3; X 2 to X 5 are a halogen atom or a hydrogen atom; R 2 to R 5 , L 1 and L 2 are a monovalent hydrocarbon group having a carbon number of 1 to 12, a monovalent aromatic hydrocarbon group, a monovalent hetero aromatic group, a halogen atom, or a hydrogen atom; one or more groups selected from R 2 to R 5 are a monovalent hydrocarbon group having a carbon number of 1 to 12, a monovalent aromatic hydrocarbon group, or a monovalent heteroaromatic group; and m is an integer of 0 or more, n is an integer of 1 or more, and m+n is an integer of 2 or more and 6 or less.
1. A method comprising:
reacting a compound represented by the following formula (1) with a compound represented by the formula R 1 —Si(CH 3 ) 3 to obtain a compound represented by the following formula (1-1A);
deprotecting the compound represented by the formula (1-1A) to obtain a compound represented by the following formula (1-1B); and
aromatizing the compound represented by the formula (1-1B);
thereby obtaining a fluorine containing aromatic compound represented by the following formula (2-1):
in the formulae, R 1 is a linear perfluoroalkyl group having a carbon number of 1 to 3;
X 2 to X 5 are a halogen atom or a hydrogen atom and they may be the same or different;
m and n are the numbers of repetitions of repeating unit structures A and B represented in parentheses, respectively, m is an integer of 0 or more, n is an integer of 1 or more, and m+n is an integer of 2 or more and 6 or less;
L 1 and L 2 are a monovalent hydrocarbon group having a carbon number of 1 to 12 which may have a substituent, a monovalent aromatic hydrocarbon group which may have a substituent, a monovalent heteroaromatic group which may have a substituent, a halogen atom, or a hydrogen atom, and they may be the same or different; in the case where m is 2 or more, a plurality of the L 1 groups present in the structure A may be the same or different and a plurality of the L 2 groups present in the structure A may be the same or different; and
in the case where at least one of m and n is 2 or more, the order of combining the structure A and the structure B may be block or random.
2. The method according to claim 1 , wherein a carbonate salt is added in the reacting step.
3. The method according to claim 1 , wherein a triphenylphosphine and a carbon tetrabromide are used in the aromatizing step.
4. The method according to claim 1 , wherein the compound represented by the formula (2-1) is a compound represented by the following formula (3-1):
5. The method according to claim 1 , wherein the compound represented by the formula (2-1) is a compound represented by the following formula (4-1) or a compound represented by the following formula (5-1):
6. A method comprising:
replacing at least one of X 2 to X 5 as halogen atom(s), in a compound where at least one of X 2 to X 5 in a compound represented by the following formula (1) is a halogen atom, by a monovalent hydrocarbon group having a carbon number of 1 to 12 which may have a substituent, a monovalent aromatic hydrocarbon group which may have a substituent, or a monovalent heteroaromatic group which may have a substituent;
reacting the compound with a compound represented by the formula R 1 —Si(CH 3 ) 3 to obtain a compound represented by the following formula (1-2A);
deprotecting the compound represented by the formula (1-2A) to obtain a compound represented by the following formula (1-2B); and
aromatizing the compound represented by the formula (1-2B);
thereby obtaining a fluorine containing aromatic compound represented by the following formula (2-1):
in the formulae, R 1 is a linear perfluoroalkyl group having a carbon number of 1 to 3;
X 2 to X 5 are a halogen atom or a hydrogen atom and they may be the same or different;
R 2 to R 5 are a monovalent hydrocarbon group having a carbon number of 1 to 12 which may have a substituent, a monovalent aromatic hydrocarbon group which may have a substituent, a monovalent heteroaromatic group which may have a substituent, a halogen atom, or a hydrogen atom; one or more groups selected from R 2 to R 5 are a monovalent hydrocarbon group having a carbon number of 1 to 12 which may have a substituent, a monovalent aromatic hydrocarbon group which may have a substituent, or a monovalent heteroaromatic group which may have a substituent; and R 2 to R 5 may be the same or different;
m and n are the numbers of repetitions of repeating unit structures A and B represented in parentheses, respectively, m is an integer of 0 or more, n is an integer of 1 or more, and m+n is an integer of 2 or more and 6 or less;
L 1 and L 2 are a monovalent hydrocarbon group having a carbon number of 1 to 12 which may have a substituent, a monovalent aromatic hydrocarbon group which may have a substituent, a monovalent heteroaromatic group which may have a substituent, a halogen atom, or a hydrogen atom, and they may be the same or different; in the case where m is 2 or more, a plurality of the L 1 groups present in the structure A may be the same or different and a plurality of the L 2 groups present in the structure A may be the same or different; and
in the case where at least one of m and n is 2 or more, the order of combining the structure A and the structure B may be block or random.
7. The method according to claim 6 , wherein a carbonate salt is added in the reacting step.
8. The method according to claim 6 , wherein a triphenylphosphine and a carbon tetrabromide are used in the aromatizing step.
9. The method according to claim 6 , wherein the compound represented by the formula (2-2) is a compound represented by the following formula (3-2):
10. The method according to claim 6 , wherein the compound represented by the formula (2-2) is a compound represented by the following formula (4-2) or a compound represented by the following formula (5-2):
11. A method comprising:
replacing at least one halogen atom of a compound represented by the following formula (2-1) where at least one of X 2 to X 5 is a halogen atom by a monovalent hydrocarbon group having a carbon number of 1 to 12 which may have a substituent, a monovalent aromatic hydrocarbon group which may have a substituent, a monovalent heteroaromatic group which may have a substituent, and
thereby obtaining a compound represented by the following formula (2-2):
in the formulae, R 1 is a linear perfluoroalkyl group having a carbon number of 1 to 3;
X 2 to X 5 are a halogen atom or a hydrogen atom and they may be the same or different;
R 2 to R 5 are a monovalent hydrocarbon group having a carbon number of 1 to 12 which may have a substituent, a monovalent aromatic hydrocarbon group which may have a substituent, a monovalent heteroaromatic group which may have a substituent, a halogen atom, or a hydrogen atom; one or more groups selected from R 2 to R 5 are a monovalent hydrocarbon group having a carbon number of 1 to 12 which may have a substituent, a monovalent aromatic hydrocarbon group which may have a substituent, or a monovalent heteroaromatic group which may have a substituent and R 2 to R 5 may be the same or different;
m and n are the numbers of repetitions of repeating unit structures A and B represented in parentheses, respectively, m is an integer of 0 or more, n is an integer of 1 or more, and m+n is an integer of 2 or more and 6 or less;
L 1 and L 2 are a monovalent hydrocarbon group having a carbon number of 1 to 12 which may have a substituent, a monovalent aromatic hydrocarbon group which may have a substituent, a monovalent heteroaromatic group which may have a substituent, a halogen atom, or a hydrogen atom, and they may be the same or different; in the case where m is 2 or more, a plurality of the L 1 groups present in the structure A may be the same or different and a plurality of the L 2 groups present in the structure A may be the same or different; and
in the case where at least one of m and n is 2 or more, the order of combining the structure A and the structure B may be block or random.
12. The method according to claim 11 , wherein the compound represented by the formula (2-1) is a compound represented by the following formula (3-1) and the compound represented by the formula (2-2) is a compound represented by the following formula (3-2):
13. The method according to claim 11 , wherein the compound represented by the formula (2-1) is a compound represented by the following formula (4-1) or a compound represented by the following formula (5-1) and the compound represented by the formula (2-2) is a compound represented by the following formula (4-2) or a compound represented by the following formula (5-2):