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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 6
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Original Articles

Chlorination of Aniline and Methyl Carbanilate by N-Chlorosuccinimide and Synthesis of 1,3,5-Trichlorobenzene

Pages 1100-1108 | Received 05 Aug 2008, Published online: 25 Feb 2009

Figures & data

Scheme 1 Reagents and conditions: a) N-chlorosuccinimide, MeCN, reflux.

Scheme 1 Reagents and conditions: a) N-chlorosuccinimide, MeCN, reflux.

Scheme 2 Reagents and conditions: a) MeOH, reflux; b) N-chlorosuccinimide, MeCN, reflux.

Scheme 2 Reagents and conditions: a) MeOH, reflux; b) N-chlorosuccinimide, MeCN, reflux.

Scheme 3 Reagents and conditions: a) N-iodosuccinimide, MeCN; b) N-chlorosuccinimide, MeCN, reflux.

Scheme 3 Reagents and conditions: a) N-iodosuccinimide, MeCN; b) N-chlorosuccinimide, MeCN, reflux.

Scheme 4 Reagents and conditions: a) 1. 70% H2SO4, NaNO2, 0 °C; b) 2. hexanes, NaH2PO2, H2O, 0 °C to rt.

Scheme 4 Reagents and conditions: a) 1. 70% H2SO4, NaNO2, 0 °C; b) 2. hexanes, NaH2PO2, H2O, 0 °C to rt.

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