3585-52-2

Usage

Uses

Used in Pharmaceutical Industry:
(2RS)-2-(4-ETHYLPHENYL)PROPANOIC ACID is used as an impurity in Ibuprofen (I140000) for its potential anti-inflammatory activities. It is important to monitor and control the levels of this impurity in Ibuprofen to ensure the safety and efficacy of the drug.
Used in Research and Development:
(2RS)-2-(4-ETHYLPHENYL)PROPANOIC ACID can be used as a research compound to study its anti-inflammatory properties and potential applications in the development of new pharmaceuticals or as a reference standard in analytical methods for the detection and quantification of impurities in Ibuprofen.

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 7495, 1990 DOI: 10.1016/S0040-4039(00)88526-3

Upstream product

• 124-38-9 carbon dioxide 
• 105-05-5 1,4-diethylbenzene 
• 132560-66-8 α-chloro-4-ethylpropiophenone 
• 56442-59-2 ethyl 2-(4-ethylphenyl)propionate 
• 100-41-4 ethylbenzene 
• 1585-07-5 1-bromo-4-ethylbenzene 
• 120-94-5 1-Methylpyrrolidine 
• 63139-21-9 4-ethylphenylboronic acid 

Relevant academic research and scientific papers

Preparation method of ibuprofen impurity N

The invention provides a preparation method of an ibuprofen impurity N, and belongs to the technical field of preparation of drug impurity standard substances, and the preparation method comprises thefollowing steps: step 1, carrying out coupling reaction

Photochemical Rearrangement of α-Chloro-Propiophenones to α-Arylpropanoic Acids: Studies on Chirality Transfer and Synthesis of (S)-(+)-Ibuprofen and (S)-(+)-Ketoprofen

A new single-step efficient photochemical approach for α-arylpropanoic acids (4) from α-chloro-propiophenones (5) is described.It involves carbonyl triplet excited state directed 1,2-aryl migration of the aryl group which has been found to be highly dependent upon the nature of the aryl substituent.The mode of the rearrangement is probed by the study of the photobehaviour of a set of optically active α-chloro-propiophenones.The results suggest that the nature of the carbonyl triplets (n, ?*/ ?, ?*) plays an important role in the chirality transfer.This method finds application in the synthesis of optically active ibuprofen (4e) and ketoprofen (26), though in moderate optical yields.

A one-pot synthesis of ibuprofene involving three consecutive steps of superbase metalation

A one-pot reaction sequence consisting of three consecutive metalation and electrophilic substitution stages leads to 2-(4-isobutylphenyl)propanoic acid with 52% over-all yield. A crucial step is the alkylation of deprotonated p-ethyltoluene with isopropyl bromide. In general terms, sec-alkyl halides and benzyl or allyl type alkalimetal reagents undergo coupling reactions with surprising ease.

Process for the preparation of α-arylalkanoic acids

α-Arylalkanoic acids are prepared by a method comprising the step of reacting an alkylaromatic compound corresponding to the desired α-arylalkanoic acid with a new metallation reagent solution. The reagent comprises the reaction product of alkyllithium or aryllithium and about two to five molar equivalents of potassium tert-alkoxide in a trialkylamine solvent.

Light-mediated direct transformation of 2-chloropropiophenones into 2-arylpropionic acids

A strategy based on photochemical 1,2-aryl migration as the pivotal step allows efficient transformation of 2-chloro-propiophenones into 2-arylpropionic acids. A noticeable substituent-directed excited state control on the rearrangement process has been observed.