Bromacetic acid

Boiling-point method, 37 determination of, 58 correction for, 59 / 1 iroinacetanilicle, 152 Bromacetic acid, 8g Broiiiaceiyl bromide, 89 Bromuhenzene, 140 y /-Bromobenz.oic acid, 201 Brouiocresol, 165 / Bromoioluene, 167 Butyric acid, 99... 

Phenyl ethyl selenide, C6H5.Se.C2H5.3—Phenyl selenide (10 grams) is dissolved in one equivalent of sodium hydroxide in the minimum of water, 50 c.c. of absolute alcohol then added, followed by 20 grams of ethyl bromide. The mixture is heated under reflux for fifteen minutes, then diluted with four times its volume of cold water, extracted three times with ether, the extract washed with water, dried over calcium chloride and distilled. Rectification of the oil obtained gives a 72 per cent, yield of the required selenide, boiling at 214° to 216° C. Treatment with bromacetic acid converts the selenide into phenyl-selenoglycollic acid.4... 

Diphenyl-telluretin bromide, (C6H5)2Te(Br).CH2.COOH, is the condensation product of diphenyl telluride and bromacetic acid, but has not been isolated in the solid state. The chloride, picrate and platinichloride have not been obtained in a pure state. 

I.G. Farben produced only the warning substance, bromacetic acid methyl ester, as well as the stabilizer, chlor carbonic acid methyl ether. 

According to Mueller ethylbromacetate is prepared by the brom-ination of acetic acid in the presence of red phosphorus and the nubse-quent esterification with alcohol of the bromacetic acid obtained. 

Ethylbromacetate. In 1858, Perkin and Duppa combined bromacetic acid and ethanol to form ethylbromacetate. This compound earlier found service by French constables in 1912 to incapacitate criminals and expedite their capture. Officially the first combat gas employed in World War I, ethylbromoacetate was delivered in the form of rifle grenades (26 millimeters) by France in... 

The previously published results [142, 143] devoted to the synthesis of thiazolo [3,2-a]imidazol-2-ones attracted attention of Krasovskii et al. [144] to synthesize corresponding ylidene derivates and to investigate biological activities, promising to be interesting for the medicinal chemistry. By heating 2-aminothiazoles with ethyl bromacetate and a variety of aromatic aldehydes at the appropriate temperature (either 80°C or reflux) in the glacial acetic acid with anhydrous sodium acetate, ylidene derivates of structures 102-104 were isolated (Scheme 48). 

The interaction of diaryl tellurides and the esters of halogenated fatty acids, e.g. methyl bromacetate, gives diarvl-telluretin halide alkyl esters, e.g. (C6H5)2Te(Br).CH2.COOCH3. The halogen present may be chlorine, bromine or iodine, moist silver oxide replacing the bromine by the hydroxyl group. 

Oxalyl-acetic ester (20 gms.) is mixed with mono-bromacetic ester (17 gms.) in a flask of 300 c.c, capacity, fitted with an air-condenser. Enough zinc turnings to cover the end of a spatula are added and the mixture becomes brown, while the temperature quickly reaches 50° and the zinc dissolves. Addition of a second portion of zinc is attended by boiling and the reaction is moderated by cooling the metal is added in excess, and the mixture is then heated on the water-bath for a short time. After cooling, the mixture is treated with cold dilute sulphuric acid and ether, well shaken to get a clear solution, and the ethereal layer removed, washed with dilute sodium carbonate and dried over calcium chloride. The ether is next distilled and the remaining oil fractionated under reduced pressure most of it passes over below 200° at 35 mm. That portion taken as citric ester (b.p, 212°—216°) is hydrolysed... 

Hexaphenols 47-49 are water-soluble at pH > 12. On alkylation with methyl bromacetate they were converted to hexaesters 50-52, followed by hydrolysis to yield hexaacids 53-55. These hexaacids are soluble in water at pH > 5 (less than 6 equivalent amounts of base added). Alternatively [20], on reaction with methylamine, followed by reduction of the intermediate hexaamide, hexaester 51 was converted to the corresponding hexaamine 56. The latter is soluble in mildly acidic water. 

Ethyl bromacetate ( C H,0sBr ) + Butyric acid ( CgHgOa ) 1-Naphthyl acetate ( CiaHt 0O2 ) + Trichloracetic acid Kendall and Booge, 1916 ( CaHOgCl, )... 

Ethyl bromacetate Lecat, 1949 ( Ci H OgBr + Isobutyric acid ... 

A cold mixture of coned. H2SO4 and glacial acetic acid added with vigorous stirring during 45 min. below 10° to a cooled mixture of anisole and bromacetal, stirring continued for 30 min. ,a-di-p-anisyl-y -bromethane (Y 85-90%)... 

Additional Exorcists.—Other suitable bimolecular reactions -which may be studied are the following Reaction between ethyl bromacetate and sodium thiosulphate (Trans. Chcm. Soe, 190S, 87, 481) reaction between hydrogen peroxide and hydriodic acid in the presence of various catalysts (ZeiiscAer. physikal. Chcm., 1901, 37, 257) reaction between potassium persulphate and hydriodic acid (Zeitsekr. physikal. Chem., 1898, 27, 477) velocity of esterification of acids by alcohols (Zeitsehr. physikal. Chtm., 1907, 60, 728 Trans. Chem. Soe., 1910, 97, 19). 

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