Benzyl bromide CAS#: 100-39-0 - ChemicalBook

This C‐C coupling reaction was optimized for the synthesis of polybenzyls by model reactions.
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ChemInform Abstract: Synthesis of Benzyl Bromides …

An oven-dried 10 mL reaction vial equipped with a stir bar was charged with LiN(SiMe3)2 2 equiv) and the benzyl thioether (1 equiv) under a nitrogen atmosphere. A 1 mL solution (from a stock solution) of [PdCl(allyl)]2 (5 mol %) and NiXantPhos (20 mol %) in dry THF was added to the vial via a syringe. After stirring for 5 min at 24 °C, aryl bromide (2 equiv) was added to the reaction mixture. The reaction mixture was stirred for 30 min at 24 °C, quenched with three drops of H2O, diluted with 1 mL of dichloromethane, and filtered over a pad of silica. The pad was rinsed with additional dichloromethane, and the solution was concentrated under reduced pressure. The crude material was loaded onto a silica gel column and purified by flash chromatography.

1.3‐Linked polybenzyls were synthesized based on the results of the model reactions.
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One-Pot Synthesis of 1,2,3-Triazoles from Benzyl and …

The reactions of pentafluoro-, pentachloro-, polybromo-, nitro-, and p-methoxy-substituted benzyl bromides with metallic mercury, leading to the synthesis of benzyl mercury compounds, have been investigated. The ease of the reaction increases as the number of bromine atoms on the benzene ring increases. Optimum reaction conditions have been recommended; these involve use of DMF as solvent in the presence of Br ion catalysts.

These benzaldehydes and bromides are particularly useful for the preparation of new radiopharmaceuticals (e.g.
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()-β-Aryl vinyl iodides are synthesized in high yield with excellent stereoselectivity from benzyl bromides by a one-pot homologation/stereoselective elimination procedure. Convenient conditions involving the anion of diiodomethane and an excess of base provide complete consumption of the benzyl bromide and elimination from a diiodoalkane intermediate. Similar conditions provide ()-β-aryl vinyl chlorides and bromides by employing the anions of ICH2Cl or CH2Br2. The functional group tolerance and facile purification allows rapid access to a wide range of functionalized vinyl halides.

These results suggest that a variety of alkyl benzyl thioethers can be selectively coupled with aryl bromides at the benzylic position.
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A member of the class of benzyl bromides that is toluene ..

The oxidative addition reaction of Hg (into the C-Br bond) is accompanied in many cases by side products of radical origin (dibenzyls, toluenes, benzaldehydes). The smoothest reactions were encountered with polybromo- and polychlorobenzyl bromide substrates.

Synthesis of polybenzyls by Suzuki Pd ..

An oven-dried 10 mL reaction vial equipped with a stir bar was charged with the benzyl thioether (1 equiv) under a nitrogen atmosphere. A 1 mL solution (from a stock solution) of [PdCl(allyl)]2 (5 mol %) and NiXantPhos (20 mol %) in dry THF was added to the vial via a syringe. After stirring for 5 min at 24 °C, aryl bromide (2 equiv) was added to the reaction mixture followed by slow addition of a solution of LiN(SiMe3)2 (2 equiv) in 0.5 mL of THF for 40 min. The reaction mixture was stirred for 15 min at 24 °C, quenched with three drops of H2O, diluted with 1 mL of dichloromethane, and filtered over a pad of silica. The pad was rinsed with additional dichloromethane, and the solution was concentrated under reduced pressure. The crude material was loaded onto a silica gel column and purified by flash chromatography.

Selective Synthesis of (Benzyl) ..

An oven-dried 10 mL reaction vial equipped with a stir bar was charged with KO-tBu (2 equiv) and the benzyl thioether (1 equiv) under a nitrogen atmosphere. A 1 mL solution (from a stock solution) of [PdCl(allyl)]2 (5 mol %) and NiXantPhos (20 mol %) in dry THF was added to the vial via a syringe. After stirring for 5 min at 24 °C, aryl bromide (2 equiv) was added to the reaction mixture. The reaction mixture was stirred for 30 min at 50 °C, cooled to room temperature, quenched with three drops of H2O, diluted with 1 mL of dichloromethane, and filtered over a pad of silica. The pad was rinsed with additional dichloromethane and the solution was concentrated under reduced pressure. The crude material was loaded onto a silica gel column and purified by flash chromatography.

Synthesis And Identification Of Alkyl Bromides From Unknown Alcohols

A direct benzylic oxidation of alkylarenes via C–H bond abstraction was developed using alkali metal bromides and oxidants under mild conditions. This reaction proceeded with excellent selectivity by thermal oxidation or photooxidation to provide a broad range of carbonyl compounds containing electron-deficient aryl carbonyl compounds in high yields.