CC BY-ND-NC 4.0 · SynOpen 2017; 01(01): 0143-0146
DOI: 10.1055/s-0036-1590959
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Ball-Milling Promoted Monobromination Reactions: One-pot Regioselective Synthesis of Aryl Bromides and α-Bromoketones by NBS and Recyclable MCM-41-SO3H at Room Temperature

N. Ghanbari
,
,
H. R. Esmaili Zand
,
M. Eslami
Further Information

Publication History

Received: 09 August 2017

Accepted after revision: 23 October 2017

Publication Date:
16 November 2017 (online)


Abstract

An effective approach to monobromination reactions utilizing room temperature ball-milling is introduced for the synthesis of aryl bromides and bromoketones with N-bromosuccinimide (NBS) and MCM-41-SO3H. Advantages of this technique are short reaction times and high regioselectivity. In contrast to other techniques using microwaves, ultrasound, or ionic liquids, handling of sensitive materials is possible and furthermore, this method has advantages over other solvent-free techniques that require a higher reaction temperature for high yield of products.

Supporting Information

 
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  • 48 Preparation of MCM-41-SO3H: Diethylamine (2.7 g) was added to deionized water (42 mL) at room temperature. The mixture was stirred for 10 min, then cetyltrimethylammonium bromide (1.47 g) was added and the mixture was stirred for 30 min until a clear solution was obtained. To this mixture, tetraethoxysilane (2.1 g) was added dropwise and the pH of the reaction mixture was maintained at 8.5 by adding hydrochloric acid solution (1 M). After 2 h, the solid product was filtered, washed with deionized water, dried at 45 °C for 12 h, and then calcined at 550 °C for 5 h
  • 49 Preparation of MCM-41-SO3H: Dichloromethane (5 mL) containing MCM-41 (1.0 g) was added to a flask equipped with a pressure equilibrating dropping funnel charged with chlorosulfonic acid (2 mL) and equipped with a gas inlet tube. The chlorosulfonic acid was added dropwise over 30 min at room temperature and HCl gas generated was swept from the reaction vessel. The mixture was then stirred for 30 min and the solvent was evaporated to obtain MCM-41-SO3H
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