1734-77-6

Usage

Chemical Structure

CH2=CHCOOCH2CH3

Synthesis

Derived from acrylic acid and 2,6-dichlorophenol

Primary Use

Intermediate in pharmaceutical and agrochemical production

Other Uses

Synthesis of organic compounds
Reagent in organic synthesis
Building block for compound preparation

Safety Concerns

Flammable
May cause skin, eye, and respiratory irritation upon exposure

Upstream product

• 1071-46-1 hydrogen ethyl malonate 
• 83-38-5 2,6-dichlorobenzaldehyde 
• 140-88-5 ethyl acrylate 
• 541-73-1 1,3-Dichlorobenzene 

Downstream Products

• 1734-76-5 3-(2.6-Dichlor-phenyl)-prop-2-en-1-ol 
• 1507-89-7 3-Chlor-1-(2,6-dichlor-phenyl)-prop-1-en 
• 14573-24-1 3-(2,6-dichlorophenyl)-1-propanol 

Relevant academic research and scientific papers

S,O-Ligand-Promoted Palladium-Catalyzed C-H Functionalization Reactions of Nondirected Arenes

Pd(II)-catalyzed C-H functionalization of nondirected arenes has been realized using an inexpensive and easily accessible type of bidentate S,O-ligand. The catalytic system shows high efficiency in the C-H olefination reaction of electron-rich and electron-poor arenes. This methodology is operationally simple, scalable, and can be used in late-stage functionalization of complex molecules. The broad applicability of this catalyst has been showcased in other transformations such as Pd(II)-catalyzed C-H acetoxylation and allylation reactions.

Ligand-accelerated non-directed C-H functionalization of arenes

The directed activation of carbon-hydrogen bonds (C-H) is important in the development of synthetically useful reactions, owing to the proximity-induced reactivity and selectivity that is enabled by coordinating functional groups. Palladium-catalysed non-directed C-H activation could potentially enable further useful reactions, because it can reach more distant sites and be applied to substrates that do not contain appropriate directing groups; however, its development has faced substantial challenges associated with the lack of sufficiently active palladium catalysts. Currently used palladium catalysts are reactive only with electron-rich arenes, unless an excess of arene is used, which limits synthetic applications. Here we report a 2-pyridone ligand that binds to palladium and accelerates non-directed C-H functionalization with arene as the limiting reagent. This protocol is compatible with a broad range of aromatic substrates and we demonstrate direct functionalization of advanced synthetic intermediates, drug molecules and natural products that cannot be used in excessive quantities. We also developed C-H olefination and carboxylation protocols, demonstrating the applicability of our methodology to other transformations. The site selectivity in these transformations is governed by a combination of steric and electronic effects, with the pyridone ligand enhancing the influence of sterics on the selectivity, thus providing complementary selectivity to directed C-H functionalization.