benzyl bromide

Electrophilic trapping is carried out under standard conditions in the presence of an electrophile such as benzyl bromide.

Protection: Potassium hydride, tetra-n-butylammonium iodide, and benzyl bromide.

The treatment with bromine in the presence of benzoyl peroxide leads to the formation of the corresponding benzyl bromide.

Benzyl bromide, or α-bromotoluene, is an organic compound consisting of a benzene ring substituted with a bromomethyl group.

The use of mixed zinc/copper organometallic reagents generated from benzyl bromides represents a second alternative to lateral lithiation.

Benzyl bromide is a strong lachrymator and is also intensely irritating to skin and mucous membranes.

Benzyl bromide can be synthesized by the bromination of toluene under conditions suitable for a free radical halogenation:

Toluene can also be treated with elemental bromine in the presence of UV light (direct sunlight) to yield benzyl bromide.

Benzyl bromide is used in organic synthesis for the introduction of the benzyl protecting group for alcohols and carboxylic acids.

For example, N-bromosuccinimide (NBS) heated with toluene in the presence of AIBN leads to benzyl bromide.

In another development, Anet and Leblanc also in 1957 prepared a benzyl chromium solution from benzyl bromide and chromium(II) perchlorate.

It is preferable over benzyl bromide for the preparation of benzylic Grignard reagent, since the reaction of the bromide with magnesium tends to form the Wurtz-coupling product 1,2-diphenylethane.

In this case, the cyanide anion is the synthetic equivalent for the COOH synthon, while benzyl bromide is the synthetic equivalent for the benzyl synthon.

The thus generated 2-lithio-1,3-dithiane reacts as a nucleophile in nucleophilic displacement with alkyl halides such as benzyl bromide, with other carbonyl compounds such as cyclohexanone or oxiranes such as phenyl-epoxyethane, shown below.

They examined the chemical kinetics for the reaction of pyridine with benzyl bromide and with a range of benzyl bromides with different para alkyl substituents (reaction product a pyridinium salt).

The original 1928 publication by T.S. Stevens concerned the reaction of 1-phenyl-2- (N, N-dimethyl) ethanone with benzyl bromide to the ammonium salt followed by the rearrangement reaction with sodium hydroxide in water to the rearranged amine.

Hans Tappen, a chemist in the Heavy Artillery Department of the War Ministry, suggested to his brother, the Chief of the Operations Branch at German General Headquarters, the use of the tear-gases benzyl bromide or xylyl bromide.