Publication

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

Manfred Schlosser
1991
Journal Articles

Abstract

A one-pot reaction sequence consisting of three consecutive metalation and electrophilic substitution stages starting with p-xylene leads to 2-(4-isobutylphenyl)propanoic acid with a 52% overall 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 alkali metal reagents undergo coupling reactions with surprising ease. [on SciFinder (R)]

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Manfred Schlosser
1991
Journal Articles

Abstract

Official source

Related concepts (24)

Organolithium reagent

In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers.

Alkyl group

In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula . Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula .

Chemical synthesis

In chemistry, chemical synthesis (chemical combination) is the artificial execution of chemical reactions to obtain one or several products. This occurs by physical and chemical manipulations usually involving one or more reactions. In modern laboratory uses, the process is reproducible and reliable. A chemical synthesis involves one or more compounds (known as reagents or reactants) that will experience a transformation when subjected to certain conditions. Various reaction types can be applied to formulate a desired product.

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

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