Phenoxyethyl Bromide

The quaternary ammonixim salt 73, thenium closylate, is an anthelmintic agent. Many substances of this general type are effective by interfering with nervous conduction, and thereby muscle tone, of intestinal worms. This allows their expulsion, not always in the dead state. The synthesis proceeds from 2-thienylamine (70) by monoalkylation with 2-phenoxyethyl bromide (71) to give secondary amine 72. 

Phe oxye1ihyl bromide may be made in a similar manner. Two kilos of ethylene bromide, 285 g. of phenol and 2 1. of water, upon treatment with 375 g. ot sodium hydroxide, yield 960-970 g. of phenoxyethyl bromide (54-57 per cent of the theoretical amount) boiling at i25-i30°/i8 mm. 

Two techniques are commonly used in the preparation of olefinic ethers from halo ethers. The first involves heating a /5-halo ether with fused or powdered potassium hydroxide. This method is typified by the conversion of -phenoxyethyl bromide to phenyl vinyl ether (69%) and, /5 -dichlorodiethyl ether to divinyl ether (61%). In the latter case, yields are improved in the presence of ammonia gas. In the second procedure, an aliphatic or aromatic chloro ether is heated with pyridine to 115°. This method is of value in the preparation of several methoxystyrenes. Chloroalkylation of the aromatic ether is followed by dehydrohalogenation. 

They are obtained by condensing benzyl chloride or its substitution products with sodium jp-arsanilate. Using phenoxyethyl bromide or its derivatives, the condensation products are of the type... 

Vinyl Pentachlorophenyl Ether, (9). Method A 2-Pentachlo-phenoxyethyl bromide (0.4 g, 1.1 mmol) was dissolved In tetrahydrofuran (3 ml) and l,5-dlazablcyclo-5,4,0-undec-5-ene (DBU) (0.16 g, 1.1 mmol) was added dropwlse to the solution. The mixture was refluxed for 30 minutes and water (100 ml) was added, and the solution was extracted with chloroform. The chloroform extract was dried with anhydrous MgS04 and the chloroform removed In vacuo to yield 0.2 g (64.5%) of (9). 

The starting material for bephenium salts is 2-phenoxyethyl bromide (42), which may be converted into bephenium either in one or two steps as shown in scheme 2 [4-9]. 

Dodecanaminium, IM,N-dimethyl-N-(2-phenoxyethyl)-, bromide. SeeDomiphen bromide... 

CAS 538-71-6 EINECS/ELINCS 208-702-0 Synonyms N,N-Dimethyl-N-(2-phenoxyethyl)-1 -dodecanaminium bromide 1-Dodecanaminium, N,N-dimethyl-N-(2-phenoxyethyl)-, bromide Dodecyidimethyl (2-phenoxyethyl) ammonium bromide PDDB Phenododecinium bromide P-Phenoxyethyidimethyidodecylammonium bromide... 

Prepared from phenoxyethyl bromide (559) and malonic ester by the procedure of Fischer and Blumenthal (293). o-Amino-y-butyrolactone hydrochloride has been prepared from y-butyrolactone through the o-bromo-y-butyrolactone lavak et cl. (521), by reduction of crroximino> y-but3rrolaotone with tin and HCl (450) or with Baney Nickel and hydrogen (450). The intermediate o-acetamino-y-butyrolactone was hydrolysed by the method of Hill and Robson (400). 

A mixture of theophylline, -phenoxyethyl bromide, and NaOH in water-ethanol refluxed 9 hrs. 7-y -phenoxyethyltheophylline (Y 90%) refluxed 25 hrs. with... 

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