Ethers alkyl bromomethyl

If paraformaldehyde (30 g) and an alcohol (1 mole) are allowed to react with HBr (1 mole), addition of CaCl2 (1 mole) leads to increased yields of alkyl bromomethyl ethers.992... 

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. ... 

Iron-acyl enolates, such as 2, prepared by x-deprotonation of the corresponding acyl complexes with lithium amides or alkyllithiums, are nearly always generated as fs-enolates which suffer stereoselective alkylation while existing as the crmt-conformer which places the carbon monoxide oxygen anti to the enolate oxygen (see Section 1.1.1.3.4.1.). These enolates react readily with strong electrophiles, such as primary iodoalkanes, primary alkyl sulfonates, 3-bromopropenes, (bromomethyl)benzenes and 3-bromopropynes, a-halo ethers and a-halo carbonyl compounds (Houben-Weyl, Volume 13/9 a, p 413) (see Table 6 for examples). 

Ethyl a-(bromomethyl)acrylate has proved to be an excellent reagent for conversion of aldehydes and ketones, both acyclic and cyclic, into the corresponding a-methylene-y-butyrolactone derivatives4"9 in a Re-formatsky type reaction. The yield was excellent in the case of several spiro a-methylene-y-butyrolactones.10 Synthetic a-methylene-y-butyrolactone derivatives have been shown to possess antitumor activity.5 6,7 1112 Ethyl a-(bromomethyl)acrylate has also proven of value in the synthesis of alkylated products of enol ethers of cyclohexane-1,3-dione.13... 

The majority of 2-alkyl-5-aryl- 1,3,4-oxadiazoles can easily be cleaved in mineral acid solution to give the corresponding diacid hydrazides. 2-(a-Bromoethyl)-5-phenyl-l,3,4-oxadiazole is hydrolyzed so easily that even during the synthesis from l-a-bromopropionyl-2-benzoylhydrazine, on treating the reaction mixture with water, partial hydrolysis occurs to give the diacid hydrazide or even hydrazine.19 This can be eliminated in the synthesis by among other means the use of petrol ether in place of water. The 2-bromomethyl-5-aryl-... 

The ion-pair dissociation of ambident alkali enolates, which results in increasing 0/C alkylation ratios, can be promoted not only by dissociating solvents but also by specific cation solvation. In the latter case, EPD solvents cf. DMF and DMSO in Table 5-22b) or macro(poly)cyclic ligands such as coronands ( crown ethers ) or cryptands are used [376, 377, 660]. For example, the alkylation of sodium y9-naphtholate with (bromomethyl)benzene or iodomethane in the presence of benzo[18]crown-6 gives high O/C alkylation ratios when tetrahydrofuran or benzene are the solvents [660]. In dissociating solvents such as A,A-dimethylformamide or acetonitrile, however, so far no... 

The synthesis of non-peripherally substituted octa(alkoxymethyl)phthalocyanines is outlined in Seheme 57 [213, 214]. 2,5-fcij(Alkoxymethyl)furan can be prepared by lithiation of furan followed by quenching the anion with (bromomethyl)alkyl ether to give the mono-substituted furan, and repetition of the procedure to give the required product [213]. A more simple synthesis involves chlorination of 2,5-furan dimethanol with thionyl chloride, followed by nucleophilic displacement of chloride with sodium alkoxide [214]. The furan is equilibrated with fumaronitrile for about a week and the Diels-Alder adduct aromatized by treatment with lithium fcwftrimethylsilyl)-amide (a non-nucleophilic base), followed by an acidic work-up. The 3,6-/7i5(alkoxy-methyl)phthalonitrile is cyclized under standard conditions (lithium/pentanol). 

Intermolecular a-alkylation of aldehydes with 2-(bromomethyl)acrylates 18 were developed by the Palomo group [8]. The reaction was best catalyzed by diphenyl-prolinol TMS (6 )(Scheme 25.5) or dihexylprolinol triphenylsilyl ethers (Scheme 25.6), and required the presence of an acid scavenger, such as DABCO or DMAP. 

C12-C18 soaps alkyl distribution Sewage and sewage sludge Sludge preliminary Soxhlet extraction with petroleum ether to remove lipids, addition of Ci7 internal standard, conversion to soluble salts, Soxhlet extraction with MeOH. Sewage no workup RP-HPLC of p-bromophenacyl bromide derivative-UV detection (254 nm), or 4-bromomethyl-7-methoxy coumarin-fluorescence detection (X xAem = 328/380 nm) 45,176,177... 

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