54625-53-5

Usage

InChI:InChI=1/C9H11ClO3/c1-11-7-5-4-6(10)8(12-2)9(7)13-3/h4-5H,1-3H3

Upstream product

• 128-09-6 N-chloro-succinimide 
• 634-36-6 1,2,3-trimethoxybenzene 
• 507-40-4 tert-butylhypochlorite 
• 18113-22-9 3-chloro-2,6-dimethoxyphenol 
• 77-78-1 dimethyl sulfate 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 3598-34-3 4-Chloro-1,2,3-trihydroxybenzene 

Downstream Products

• 98993-61-4 1-chloro-2,3,4-trimethoxy-5,6-dinitro-benzene 

Relevant academic research and scientific papers

In Situ Formed IIII-Based Reagent for the Electrophilic ortho-Chlorination of Phenols and Phenol Ethers: The Use of PIFA-AlCl3 System

A new and in situ formed reagent generated by mixing PIFA {bis[(trifluoroacetoxy)iodobenzene]} and AlCl3 was introduced in the organic synthesis for the direct and highly regioselective ortho-chlorination of phenols and phenol ethers. An efficient electrophilic chlorination for these electron-rich arenes as well as the scope of the reaction are described herein. An easy, practical, and open-flask reaction allowed us to introduce a chlorine atom, which is a highly important functional group in organic synthesis. The reproducibility of our method has been demonstrated on gram-scale by carrying out the reaction in 6-bromo-2-naphthol. This halogenation reaction also proceeds in excellent conditions by first preparing the iodine(III)-based chlorinating reagent. Our new chlorinating reagent can be stored at least for two weeks at 4 °C without losing its reactivity.

Efficient halogenation of aromatic systems using N-halosuccinimides in ionic liquids

A simple, rapid and highly regioselective green protocol has been developed for the halogenation of aromatic systems with N-halosuccinimides using room temperature ionic liquids (ILs) as novel and recyclable reaction media to produce the corresponding halogenated aromatic compounds in high to quantitative yields. N-Halosuccinimides show enhanced reactivity in ionic liquids thereby reducing the reaction times dramatically and improving the yields substantially.

Kaolin-assisted Aromatic Chlorination and Bromination

Moist kaolin catalyses the regioselective and high-yielding chlorination and bromination of C6H5OR (R = C1-C8 alkyl. Bu1, allyl, cyclohexyl, benzyl) to 4-XC6H4OR (X = Cl and Br, respectively) with NaCl02 and Mn(acac)3 in CH2Cl2 in the absence and presence of NaBr, respectively, under mild and neutral conditions.

Selective aromatic chlorination of activated arenes with sodium chlorite, (salen)manganese(III) complex, and alumina in dichloromethane

The reaction of alkyl phenyl ethers with sodium chlorite in dichloromethane in the presence of a (salen)manganese(III) complex and alumina preloaded with a small amount of water afforded monochlorination products with unusually high para selectivities under mild conditions. The NaClO2-based biphasic system can also be successfully used for the regioselective monochlorination of substituted anisoles and polymethoxybenzenes.

Regiospecific aromatic chlorination of alkyl phenyl ethers using sodium chlorite catalysed by manganese(III) acetylacetonate and moist alumina in dichloromethane

A solid-liquid biphasic system (dichloromethane and chromatographic neutral alumina) has been tested for the aromatic chlorination of various alkyl aryl ethers using a reagent combination of sodium chlorite and manganese(III) acetylacetonate catalyst. Efficient incorporation of a chlorine atom into the benzene ring with high para-selectivity results. This catalytic system is also applicable to the regiocontrolled chlorination of polyether substrates.