Method of manufacturing an aminoaryl-containing organosilicon compound and method of manufacturing an intermediate product of the aforementioned compound
View Patent ↗To provide an aminoaryl containing organosilicon compound with high efficiency, after protecting amino groups of a haloaniline compound with a specific compound, to form a Grignard reagent and to deprotect the aforementioned groups by reacting the Grignard reagent with a silicon compound.
1. A method of manufacturing an organosilicon compound of general formula (1):
where,
R 1 , R 2 , R 3 , and R 4 independently represent alkyl groups with 1 to 4 carbon atoms;
R 5 represents an alkylene group with 1 to 6 carbon atoms;
R 6 , R 7 , R 8 , and R 9 independently represent a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or an alkoxy group with 1 to 4 carbon atoms;
R 10 represents a univalent hydrocarbon group;
Y represents an alkoxy group having from 1 to 4 carbon atoms;
n is an integer from 1 to 4; and
m is an integer from 1 to n,
said method being characterized by causing a reaction between a compound of general formula (2):
where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are the same as defined above, and X designates a halogen atom, and an active metal or a metalloorganic compound of general formula (3):
R 11 MX (3)
where R 11 is a univalent hydrocarbon group, M is a bivalent metal, and X is a halogen atom, thus preparing a Grignard compound of general formula (4):
where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , M, and X are the same as defined above, and then causing a reaction between the obtained Grignard compound and an organosilicon compound of general formula (5):
Y n SiR 10 4-n (5)
where Y, R 10 , and n are the same as defined above.
2. A method as set forth in claim 1 wherein R 5 represents an ethylene group.
3. A method as set forth in claim 1 wherein m is 1 and n is greater than 1.
4. A method as set forth in claim 1 wherein m is equal to n.