6641-04-9

Usage

InChI:InChI=1/C8H9ClO/c1-5-3-6(2)8(10)7(9)4-5/h3-4,10H,1-2H3

Upstream product

• 1198-37-4 2,4-dimethylquinoline 
• 105-67-9 2,4-Xylenol 
• 7647-01-0 hydrogenchloride 
• 51770-93-5 4-hydroxy-2,4-dimethyl-2,5-cyclohexadienone 
• 64-19-7 acetic acid 
• 861551-31-7 4-hydroxy-2,4-dimethyl-5-(N'-phenyl-hydrazino)-cyclohex-2-enone 

Downstream Products

• 855403-60-0 6-chloro-3-chloromethyl-2,4-dimethyl-phenol 
• 132982-43-5 2-(2-chloro-4,6-dimethyl-phenoxymethyl)-5-methoxy-pyran-4-one 
• 85033-98-3 4,6-dichloro-2,4-dimethylcyclohexa-2,5-dienone 
• 1131890-99-7 2-chloro-4,6-dimethylphenyl nonaflate 

Relevant academic research and scientific papers

Modular synthesis of indoles from imines and o-dihaloarenes or o-chlorosulfonates by a Pd-catalyzed cascade process

A detailed study of the scope of a new Pd-catalyzed synthesis of indolesfrom 1,2-dihaloarenes and o-halobenzene sulfonates and imines is descri bed. The cascade reaction comprises an imine a-arylation ollowed by an intramolecular C-N bond-forming reaction promoted by the same Pd catalyst. The reaction with 1,2-dibromobenzene shows wide scope and allows the introduction of aryl, alkyl, and vinyl substituents at different positions of the five-membered ring of the indole. The regioselective synthesis of indoles substituted in the six-membered ring can be carried out by employing o-dihalobenzene derivatives with two different halogens, taking advantage of the different reactivities of I, Br, and Cl in oxidative addition reactions. This paper also introduces a method for the efficient cleavage of the N-t-butyl group, thus allowing for the preparation of N-H indoles through the same methodology. Finally, the reaction with o-halosulfonates has been studied. The best substrates are o-chlorononaflates, which lead to indoles in very high yield. The reaction is particularlyappropriate for the synthesis of the challenging 6-substituted indoles. In view of the availability of o-chlorophenols, which are direct precur sors of the chlorononaflates, this reaction represents an efficient entry into indoles substituted in the six-membered ring. The concept is illustrated by the preparation of a 4,6-disubstituted indole from naturally occurring anethole.

Electrophilic Chlorination of 4-Methylphenols with Molecular Chlorine. Synthesis of Dimethoxy Aromatics by Methanolysis of 4-Chloro-4-methylcyclcohexa-2,5-dienones

The chlorination of p-cresol (1a), 2,4-dimethylphenol (1b), 3,4-dimethylphenol (1c), 2,4,5-trimethylphenol (1d), 2,4,6-trimethylphenol (1e) and the various possible mono- and dichloro derivatives of these phenols (3a-d, 6a and 6 c) with molecular chlorine was investigated in dichloromethane or dimethyl formamide solution.The 2,6-substituted p-cresol derivatives all give quantitative yields of 4-chloro-4-methylcyclohexa-2,5-dienones (5b, 5d, 7a, 7c and 2e), whereas the less substituted p-cresol derivatives give a 20-25percent yield of corresponding 4-chloro-4-methylcyclohexa-2,5-dienones (2a-d, 5a and 5c), the other products being chlorinated phenols.Treatment of 4-chloro-4-methylcyclohexa-2,5-dienones with at least one of the double bonds of the ring unsubstituted (2a-c and 4a) with methanol gave a quantitative yield of a 1,3-dimethoxybenzene derivative (9a-c and 10), whereas similar treatment of 4-chloro-2,4,5-trimethylcyclohexa-2,5-dienone (2d) gave 5-methoxy-2,3-dimethylbenzyl methyl ether (11).Treatment of the other 4-chlorodienones with methanol gave the corresponding 4-methoxydienones.Electrophilic chlorination of certain p-cresol derivatives followed by methanolysis hence is a facile although low-yield method for 3-methoxylation or selective side chain oxidation of these p-cresol derivatives.