Benzyl bromomethyl ether

Several other alkylation reactions of benzyl chloromethyl ether have been reported using phosphorus compounds as nucleophiles. Hydrolysis and alcoholysis reactions of the reagent have been investigated along with the addition of the chloroether to propylene in the presence of zinc chloride. The alkylation of enamines with benzyl bromomethyl ether has been reported. ... 

A chiral [4]pseudocatenane 16 was synthesized from chiral triptycene-based /m( crown ether) and three equivalents of hw[p-(but-3-enyloxy)benzyl]ammonium salt in CH2CI2 in the presence of Grubbs II catalyst, followed by reduction <06CEJ5603>. Several novel calix[4]arenocrowns were prepared by a simple one-pot reaction of calix[4]monohydroquinone diacetate with bw-tosylates, e.g. l,4-bw[2-(2-(2-(2-tosyloxy-ethoxy)ethoxy)ethoxy)ethoxy)benzene, in dry MeCN in the presence of NaOH the self-assembly into calix[4]areno[2]catenanes with a dicationic salt and />-bfr(bromomethyl)-benzene was also demonstrated <06TL6012>. 

BRN 1912585, see Hexachlorobenzene BRN 1912384, see 2,4-Dinitrotoluene BRN 1913355, seep,p -DDE BRN 1914064, see Di-fl-butyl phthalate BRN 1914072, see p,p -DDD BRN 1915474, see Chlordane BRN 1915994, see Di-fl-octyl phthalate BRN 2049930, see Naled BRN 2051258, see Pindone BRN 2052046, see 2,6-Dinitrotoluene BRN 2054389, see 4,6-Dinitro-o-cresol BRN 2055620, see 2,4,5-T BRN 2057367, see Methoxychlor BRN 2059093, see Parathion BRN 2062204, see Benzyl butyl phthalate BRN 2215168, see Diuron BRN 2542580, see EPN BRN 2807677, see 2-Acetylaminofluorene BRN 3195880, see a-BHC BRN 3196099, see Camphor BRN 3910347, see cis-Chlordane, frans-Chlordane Brocide, see 1,2-Dichloroethane Brodan, see Chlorpyrifos Bromchlophos, see Naled Bromex, see Naled Bromic ether, see Ethyl bromide Bromobenzol, see bromobenzene 4-Bromobiphenyl ether, see 4-Bromophenyl phenyl ether 4-Bromodiphenyl ether, see 4-Bromophenyl phenyl ether p-Bromodiphenyl ether, see 4-Bromophenyl phenyl ether Bromoethane, see Ethyl bromide Bromofluoroform, see Bromotrifluoromethane Bromofume, see Ethylene dibromide Brom-o-gaz, see Methyl bromide Bromomethane, see Methyl bromide Bromomethyl chloride, see Bromochloromethane... 

Isoindoles can be produced by eliminations from A-substituted isoindolines (1,3-dihydro-isoindoles), themselves readily produced by the reaction of a nitrogen nucleophile and a l,2-bis(bromomethyl)-benzene examples are the pyrolytic eUmination of acetic acid from the cyclic hydroxylamine acetate,or, at a much lower temperature, of benzyl alcohol from an A-hydroxy-isoindoline benzyl ether, or of methanesulfonic acid from a corresponding mesylate. A-substituted isoindoles, too, have generally been made from an isoindoline by elimination processes, thus A-oxides can be made to lose water by pyrolysis," or better, by treatment with acetic anhydride. ... 

Hydroxymethyl to Bromomethyl Groups 380,448 ArCH2OH -> ArCH2Br Benzyl Ethers to Alcohols 442 ArOBn -> ArOH... 

For addition of HOBr the unsaturated compound is usually stirred for some hours at room temperature with bromine water, then the excess of hypobromite is removed by sodium hydrogen sulfite, the solution is saturated with salt, and the bromohydrin is shaken out of the aqueous phase into ether or CHC13. A cold solution of hypobromite obtained from bromine and alkali carbonate may be used in place of bromine water.281 The tendency of styrene to bromohydrin formation is so great that -(bromomethyl)benzyl alcohol is obtained in excellent yield even in hot water (60-90°) by use of a bromine solution in the presence of KBr.261 282... 

Bromomethylation is also possible, e.g.y the preparation of benzyl bromide in 86.5% yield from benzene, formaldehyde, and hydrogen bromide in acetic plus sulfuric acid.684,685 So is iodomethylation of aromatic compounds, by reaction of bis(chloromethyl) ether and hydrogen iodide in glacial acetic acid.686... 

In Scheme 12 the synthesis of an expanded optically active phosphine is shown. The preparation of the P substituents starts from l-bromo-3,5-dimethylbenzene which is converted into the bis(bromomethyl)bromoxylene by MBS, depicted in the upper left comer of Scheme 12. Reaction with the Na derivative of menthol forms the ether bonds to the menthyl groups starting from the benzylic positions. In the reaction with BuLi, a metal halogen exchange with the bromine substituent of the aromatic ring is the next step. Addition of CI2P-CH2-CH2-PCI2 completes the synthesis. The new... 

Benzyl isobutyrate 810 Bis(2-ethoxyethyl) ether 3440 2-(Bromomethyl)-l/f-isoindole- ... 

This protocol recently rose in appeal by the observation of Gau et al. that 4 mol% of cheap [NiCl2(PPh3)2] catalyzes such aryl-alkyne couplings with an even higher efficiency [146]. Moreover, various benzyl bromides as well as bromomethyl-substituted heteroarenes were alkynylated in yields exceeding 90% when diethyl ether was used as the solvent. These nickel-catalyzed benzyl-alkynyl couplings... 

Similar structures can also be prepared using ATRP chemistry and in this case the initiating group is simply a chloromethyl or bromomethyl species at a focal point [204], Linear poly (acrylate) and poly (acrylic acid) blocks [205,206] are then connected to the dendrimer at its core. They were prepared by the copper-catalyzed living radical polymerizations of acrylates with dendrimer-type macroinitiators having a benzyl bromide at the focal point. After hydrolysis, amphiphilic block copolymers with a linear PAA hydrophilic block and a dendritic poly (benzyl ether) as hydrophobic block were obtained [205,206]. 

---