US 12,215,065 B2
Methods for producing arylamine compound and electrophotographic photosensitive member
Naohiro Takahashi, Chiba (JP); Koichi Nakata, Tokyo (JP); and Takuya Kosukegawa, Chiba (JP)
Assigned to Canon Kabushiki Kaisha, Tokyo (JP)
Filed by CANON KABUSHIKI KAISHA, Tokyo (JP)
Filed on Oct. 18, 2022, as Appl. No. 18/047,305.
Claims priority of application No. 2021-177592 (JP), filed on Oct. 29, 2021.
Prior Publication US 2023/0136697 A1, May 4, 2023
Int. Cl. C07C 209/78 (2006.01); G03F 7/031 (2006.01)
CPC C07C 209/78 (2013.01) [G03F 7/031 (2013.01)] 15 Claims
 
1. A method for producing an arylamine compound represented by formula (C), the method comprising an addition reaction, as a Friedel-Crafts reaction, of adding a chemical compound represented by formula (B) to a carbon atom bonded to a hydrogen atom on a benzene ring of a chemical compound represented by formula (A), in the presence of one or more acids selected from the group consisting of Lewis acids and sulfonic acids, to produce the arylamine compound:

OG Complex Work Unit Chemistry
wherein:
in the formula (A), Ra1, Ra2, Ra3, Ra4, and Ra5 each independently represent a hydrogen atom or an alkyl group, at least one of Ra1, Ra2, Ra3, Ra4, and Ra5 is the hydrogen atom, and RaA and RaB each independently represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, an acyl group, or an oxycarbonyl group;
in the formula (B), Rb1, Rb2 and Rb3 each independently represent a hydrogen atom or a methyl group, Rb4 represents a hydrogen atom, a hydroxy group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted aryloxy group, and * represents a carbon atom position bonding with the formula (A); and
in the formula (C), Rc1, Rc2, Rc3, Rc4, and Rc5 each independently represent a hydrogen atom, an alkyl group, or a monovalent group represented by formula (D), such that at least one of Rc1, Rc2, Rc3, Rc4, and Rc5 is the monovalent group represented by the formula (D), and RcA and RcB each independently represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, an acyl group, or an oxycarbonyl group; and:

OG Complex Work Unit Chemistry
wherein, in the formula (D), Rd1, Rd2, and Rd3 each independently represent a hydrogen atom or a methyl group, Rd4 represents a hydrogen atom, a hydroxy group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted amino group, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted aryloxy group, and * represents a bonding position.