79069-37-7

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-Bromo-4-methoxyphenyl)acetamide is used as an intermediate in the synthesis of various pharmaceuticals for its antimicrobial and anti-inflammatory properties. It aids in the development of new drugs to treat a range of diseases by providing a versatile building block in organic synthesis.
Used in Agrochemical Industry:
In the agrochemical sector, N-(2-Bromo-4-methoxyphenyl)acetamide serves as an intermediate in the production of compounds that possess antimicrobial properties. This application is crucial for developing solutions to combat microbial infections in agriculture, thereby enhancing crop protection and yield.

Upstream product

• 591-20-8 3-Bromophenol 
• 104-94-9 4-methoxy-aniline 
• 51-66-1 4-methoxyacetanilide 
• 67-56-1 methanol 
• 614-76-6 N-acetyl-2-bromoaniline 
• 98447-30-4 2-bromo-4-methoxy-1-nitrobenzene 
• 5470-65-5 3-bromo-4-nitrophenol 
• 32338-02-6 2-bromo-4-methoxyaniline 
• 108-24-7 acetic anhydride 

Downstream Products

• 1356388-75-4 2-(2-acetamido-5-methoxyphenyl)pyridine 1-oxide 
• 58246-80-3 1-(5-methoxy-1H-indol-1-yl)ethan-1-one 
• 6705-03-9 2-Amino-5-methoxybenzoic acid 
• 38985-80-7 2-(acetylamino)-5-methoxybenzoic acid 
• 79044-03-4 2-ethenyl-4-methoxyacetanilide 

Relevant academic research and scientific papers

Nickel(II)- And Silver(I)-Catalyzed C-H Bond Halogenation of Anilides and Carbamates

ortho -C-H bond halogenation of anilides and N -aryl carbamates using easily available N -halosuccinimides (NXS) as the active halogenation reagent in the presence of nickel or silver catalyst has been developed. This method provides a new approach to 2-haloanilides and carbamates, which may serve as starting materials for the synthesis of pharmaceutically and biologically active compounds.

Rhodium-Catalyzed ortho-Bromination of O-Phenyl Carbamates Accelerated by a Secondary Amide-Pendant Cyclopentadienyl Ligand

It has been established that a newly developed cyclopentadienyl rhodium(III) [CpARhIII] complex, bearing an acidic secondary amide moiety on the Cp ring, is able to catalyze the ortho-bromination of O-phenyl carbamates with N-bromosuccinimide (NBS) at room temperature. The presence of the acidic secondary amide moiety on the CpA ligand accelerates the bromination by the hydrogen bond between the acidic NH group of the CpA ligand and the carbonyl group of NBS.

A Visible Light-Mediated Regioselective Halogenation of Anilides and Quinolines by Using a Heterogeneous Cu-MnO Catalyst

A simple and practical heterogeneous Cu-MnO catalyzed regioselective halogenation of anilides and quinolines under irradiation with household 40 W incandescent lamp was developed. This method uses a recyclable Cu-MnO catalyst, acetonitrile as an industrially friendly solvent, and economic N-halo succinimides as a halogenating source. The reaction is scalable and well tolerated with a broad range of functional groups.

Cobalt(II)-catalyzed regioselective C-H halogenation of anilides

A cobalt-catalyzed regioselective C-H halogenation methodology is reported herein. The highlight of this work is the highly selective C-H functionalization of anilides, which results in high-yielding, versatile, and practical halogenated products. Thereby, brominations, chlorinations and iodinations of many electron-rich and electron-deficient anilides were achieved in a highly selective fashion. Mechanistic studies with respect to the pathway of the reaction are also described.

Monoprotected l-Amino Acid (l-MPAA), Accelerated Bromination, Chlorination, and Iodination of C(sp2)?H Bonds by Iridium(III) Catalysis

Halogenated arenes are important structural motifs commonly found in biologically active molecules and used for a variety of transformations in organic synthesis. Herein, we report the mono-protected l-amino acid (l-MPAA) accelerated iridium(III)-catalyzed halogenation of (hetero)anilides at room temperature. This reaction constitutes the first example of an iridium(III)/l-MPAA-catalyzed general halogenation of (hetero)arenes through C(sp2)?H activation. Furthermore, we demonstrate the potential utility of our method through its use in the synthesis of a quinolone derivative.

Synthesis of pyridine-fused perylene imides with an amidine moiety for hydrogen bonding

Pyridine-fused perylene tetracarboxylic acid bisimides (PBIs) were synthesized via Suzuki-Miyaura coupling and acid condensation. The fused PBIs with electron-donating substituents exhibited an intramolecular charge transfer interaction. One of the N-alkyl substituents was selectively removed with BBr3 to create an amidine guest binding site. A hydrogen bonding interaction with pentafluorobenzoic acid changed the absorption spectra and enhanced fluorescence.

Direct acetoxylation and etherification of anilides using phenyliodine bis(trifluoroacetate)

Treatment of various anilides with 1.5 equiv. of phenyliodine bis(trifluoroacetate) (PIFA) and 1.0 equiv. of BF3·OEt 2 in AcOH at room temperature afforded the corresponding para-acetoxylated products with high regioselectivity. In addition, this reaction could be expanded to the etherification of anilides. In the presence of 2.0 equiv. of PIFA and 2.0 equiv. of BF3·OEt2, the reaction of anilides with alcohols provided the corresponding para-etherified products in good yields. The Royal Society of Chemistry 2011.

A synthetic approach to carbazoles using electrochemically generated hypervalent iodine oxidant

Carbazoles were successfully synthesized by oxidative cyclization of the corresponding diaryl derivatives using electrochemically generated hypervalent iodine oxidant. Electron-withdrawing nitro and donating methoxy groups at the para position of the acetamide group interfered with cyclization. Glycozoline (8) was successfully synthesized in five steps with 50% overall yield.