Selective bromination of 4-chloro-1-indanone and synthesis of (4-chloro-2, 3-dihydro-1H-indene-2-yl)methanamine

The synthesis of 4-chloro-1-indanone in four steps from 2-chlorobenzaldehyde was investigated. Bromination of this compound under various conditions occurred in the cyclopentanone ring, producing mono- and dibromo derivatives. Cyanation of 2-bromo-4-chloro-1-indanone followed by reduction gave (4-chloro-2, 3-dihydro-1H-indene-2-yl)methanamine in quantitative yield.

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Bibliographic Details
Main Authors: Jasouri,S., Khalafy,J., Badali,M., Piltan,M.
Format: Digital revista
Language:English
Published: The South African Chemical Institute 2010
Online Access:http://www.scielo.org.za/scielo.php?script=sci_arttext&pid=S0379-43502010000100013
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Description
Summary:The synthesis of 4-chloro-1-indanone in four steps from 2-chlorobenzaldehyde was investigated. Bromination of this compound under various conditions occurred in the cyclopentanone ring, producing mono- and dibromo derivatives. Cyanation of 2-bromo-4-chloro-1-indanone followed by reduction gave (4-chloro-2, 3-dihydro-1H-indene-2-yl)methanamine in quantitative yield.