Publication

The metalation of fluoroanisoles: optional regioselectivity due to metal mediated control

Manfred Schlosser
1991
Journal Articles

Abstract

2- And 4-Fluoroanisole undergo hydrogen/metal exchange at the position next to the alkoxy moiety if n-BuLi or tert-BuLi is used and at the position next to the halogen atom if the stoichiometric mixt. of butyllithium and potassium tert-butoxide serves as the reagents. 3-Fluoroanisole is always attacked at the position flanked by the 2 hetero-substituents. [on SciFinder (R)]

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Manfred Schlosser
1991
Journal Articles

Abstract

Official source

Related concepts (14)

Tert-Butyllithium

tert-Butyllithium is a chemical compound with the formula (CH3)3CLi. As an organolithium compound, it has applications in organic synthesis since it is a strong base, capable of deprotonating many carbon molecules, including benzene. tert-Butyllithium is available commercially as hydrocarbon solutions; it is not usually prepared in the laboratory. tert-Butyllithium is produced commercially by treating tert-butyl chloride with lithium metal. Its synthesis was first reported by R. B. Woodward in 1941.

Halogen

The halogens (ˈhælədʒən,ˈheɪ-,-loʊ-,_-ˌdʒɛn) are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts), though some authors would exclude tennessine as its chemistry is unknown and is theoretically expected to be more like that of gallium. In the modern IUPAC nomenclature, this group is known as group (XVII) or group (VII). The word "halogen" means "salt former" or "salt maker".

N-Butyllithium

n-Butyllithium C4H9Li (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds as in the pharmaceutical industry. Butyllithium is commercially available as solutions (15%, 25%, 1.5 M, 2 M, 2.5 M, 10 M, etc.) in alkanes such as pentane, hexanes, and heptanes.

Related publications (2)

The metalation of fluoroanisoles: optional regioselectivity due to metal mediated control

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