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The Replaceonetit of Hydi*Oxyl by Bromine

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The Replaceonetit of Hydi*Oxyl by Bromine View Article Online / Journal Homepage / Table of Contents for this issue THE REPLACEMENT OF HYDROXYL BY BROMINE. 855 LXXXVIII:.- The ReplaceoneTit of Hydi*oxyl by Bromine. By WILLIAM HENRYPERKIN, jun., and JOHNLIONEL SIREONSEN. Published on 01 January 1905. Downloaded by University of Windsor 26/10/2014 01:06:14. THEmethods available for the preparation of aliphatic compounds in which several atoms of bromine are combined with different carbon atoms are few in number. It is usually assumed that a substance containing one or more hydroxyl groups may be converted into the corresponding bromo-derivatives by treatment with hydrobromic acid, or phosphorus tri- or penta-bromide, but in attempting to use this method in the preparation of bromo-derivatives for the purpose of ring synthesis unexpected difficulties were encountered. The hydroxy -groups in such polyhydric alcohols as glycerol, erythritol, mannitol, ckc., are usually only partially replaced by bromine when these alcohols are treated with hydrobroinic acid, and if, by employing higher temperatures and a large excess of the halogen acid, the attempt is made to complete the substitution, decomposition usually takes place with much charring, and the yield obtained is con- sequently very small. The same remarks apply to the use of the View Article Online 856 PERKIN AND SIMONSEN : bromides of phosphorus in such cases, the results obtained by the action of these reagents on the polyhydric alcohols being frequently most unsatisfactory." In investigating this matter, we found that a great improvement is achieved if the alcohol is first converted into the acetate and the latter is then heated with a solution of hydrogen bromide in glacial acetic acid (saturated at 0") at about 150'. By this process, which may be represented in a general way thus : R*O*C,H,O+ HBr = RBr + HO*C,H,O, the whole of the hydroxyl groups may usually be substituted by bromine, and the reaction proceeds smoothly without any separation of carbonaceous matter, consequently a good yield is obtained and the product is easily purified. We have investigated the following cases, which may serve to illustrate this process : I. Glycol diucetate is converted quantitatively into ethylene dibromide, when it is heated with ncetic-hydrobromic acid at 150". 11. GEycerol tricccetate (triacetin) is readily acted on by acetic- hydrobromic acid at 150°, and an almost quantitative yield of s-tribronzo- propawe, CH,Br*CHBr*CH,Br,is obtained. The behaviour of triacetin, when treated with a solution of hydrogen bromide in acetic acid, has lately also been investigated by R. de la Acena (Compt. rend., 1904, 139, 867), who found that at 0" and in the dark a monobromodiacetin is produced, whereas at 100' two acetyl groups are displaced with formation of a dibromomonacetin. 111. Ergthritol tetracetate reacts readily with acetic-hydrobromic acid at 1 50°, yielding s-trans-tetrabromobzct~~ze,CH,Br*CHBr*CHBr*CH,Br (m. p. llSo), and two oily substances which boil at 122-127' (25 mm.) and 164-165O (27 mm.), and which appear to consist of s-cis-tetrccbromobzctctlze and erythritol tribromohydriw, C,H,Br,*OH, Published on 01 January 1905. Downloaded by University of Windsor 26/10/2014 01:06:14. respectively. s-Tetrabromobutane had previously been prepared from erythritol by the action of phosphorus pentabromide (Colson, Bull. SOC.Cllirn., 1887, 48, 53), as well as by the following interesting indirect process. When erythritol is heated with formic acid (Henninger, Ann. Chint. * The action of hydrobromic acid on glycerol does not appear to have been in- vestigated, but, when treated with phosphorus pentabromide, glycerol yields di- bromohydrin, CH,Br*CH( OH)'CH,Br (Aschan, Bey., 1888, 21, 2890). When erythritol reacts with aqueous hydrobromic acid, it yields a dibromohydrin, C,H6Br,(OH),, and Colson (Bull. Xoe. Chirn., 1887, 48, 53) found that s.-tra.ILs- tetrabromobutane, CH,Br*CHBr,'CHBr*CH,Br, is produced in very small quantity when erythritol is treated with phosphorus pentabromide. The action of hydro- bromic acid on niannitol has been investigated by Champion (Zcitschrift, 1871, 348) and Bouchardat (Ann. Chim. Phys., 1876, [v], 6, 102), who showed that, when heated with a saturated aqueous solution of hydrogen bromide at looo, it is con- verted into a mannitoldibrornohydiiii, CBH,Br2(OH),. View Article Online THE REPLACEMENT HYDROXYL BY HROJIINE. 857 Plu~s., 1886, [vi], 7, ZlS), it yields erythrene, GH,:CH*CH:CH,, a hydrocarbon which has also been prepared by passing the vapour of fuse1 oil through a red-hot tube (Caventou, AnnaZen, 1863, 127, 93), and by distilling trimethylpyrrolidylammoniurn iodide with caustic potash (Ciamician, Magnaghi, Be?..,1886, 19, 570, and 1887,20, 3064). Erythrene combines readily with bromine, yielding a mixture of two isomeric tetrabromides, C,H,Br,, which melt respectively at 118" and 39". The former is identical with the tetrabromobutme, which we obtained from erythritol tetracetate in the manner just described. Grimaux and CloGz (Bull. Xoc. Cl~im,1887, 48, 32) have shown that this substance distils at about 260-270", and is, at the save time, partially converted iuto the isomeric tetrabromide melting at 39O, and in order to account for this they assume that change in constitution had taken place during distillation, and that the s-tetrabromobutane had been converted into a tetrabrorno-compound of the foriuula Cl-I;CBr,*CBr,*CH,. This view can hardly be accepted as correct, and it is much more probable that the two tetrabromides are cis- and ti.ans-iiiodifications : and the broiiiide iiielting at 39" is probably the cis-iiiodificzttion, since it is produced from the less fusible (trccm-)modification by the action of heat. Ciamician seems to have held a similar. view of the isomerism of these tetrabroillo-compounds, since he suggested in 1887 (Ber., 20, 3064) that their relationship may be of the same kind as that of the inactive iriodificat ions of dibroniosuccinic and tartaric acids. The constitution of erythrene, CH,:CH*CH:CH,, is proved beyond Published on 01 January 1905. Downloaded by University of Windsor 26/10/2014 01:06:14. doubt, not only by its method of forination from erythritol, but also hy the fact that it yields s-tetrabromobutane when treated with broiiiine. This hydrocarbon contains the grouping -U:C*C:C-, and i Is behaviour towards bromine seems therefore to make it an exception to the generalisation of Thiele (Art,nden, 1898, 306, 87 ; 1901, 319, 129). IV. The tetracetate 01 pe?iteytlwitol, C(C H,*O*C,H,O),, yielded interesting results, since, when heated with acetic-hydrobromic acid at 160", it was converted into s-tetrabro/rt,otetrantet?~?lZrizet~t,La~e,C(CH,Br),, but the principal product of the reaction was tribl.on.Lotrimetl~ylcarbilzyZ ncetate, (CH,Br),C*CH2*O*C,H,0, one of the acetyl groups having escaped replacement by bromine. V. In the case of wic6n~itoZ hexcbcetate, it was found impossible to replace more than five of the acetyl groups by bromine, and the product of the reaction is pewtobromohexyl acetate, C6H8Br,(0.C,H,0), VOL, LXXXVIl. 3M View Article Online 858 PERKIN AND SIMONSEN : a crystalline substance which melts at 13g3. It is remarkable with what tenacity one of the acetyl groups remains, not only in this case, but also in the case just mentioned of the tetracetate of pentaerythritol. We have also attempted to apply the method described above to the case of aromatic substances, but without success. When phenyl acetate, C6H,*O~C,H,0,for example, was heated with acetic-hydrobromic acid, profound decoinposition set in with much charring, and no trace of bromoberizene could be isolated froin the product. These negative results led us to investigate the aclion of phosphorus pentabromide at the ordinary temperature on the trihydric phenols, pyrogallol and phloroglucinol, but no substitution of hydroxyl by bromine could be observed. When the reaction was carried out in the presence of an indifferent solvent, such as benzene, pyrogallol yielded a di6ronzopyrogccZZoZ of the prolialde formula : OH which had not previously been prepared. It melts at 150" and yields a triacetyl derivative, C,HBr,(O*C2H,0),, melting at 143". Phloroglucinol, under similar conditions, is converted into tribromo- phloroglucinol : 01-1 Br()Br OH\/OH ' Br Published on 01 January 1905. Downloaded by University of Windsor 26/10/2014 01:06:14. which had previously been obtained by brominating phloroglucinol in acetic acid solution (Herzig, Jfoncctslb., 1885, 6, 885). That phosphorus pentabromide should exert such a pronounced brominating action at the ordinary temperature and in the presence of an indifferent solvent seems remarkable. s-I'ribronzopropane (Tribrornohy drin), CH,Br CH Br *CH,Br. When glycerol is digested with acetic anhydride, it is readily con- verted into diacetin, but even when a large excess of the anhydride is employed very little triacetin is produced (Seelig, Bey., 1831, 24, 3467; Geitel, J. pr. Chem., 1598, [ii], 57, 117). We have found that the following method may conveniently be used in preparing pure triacetin (compare Erwig and Koenigs, Her., 1889, 22, 1464). Glycerol (20 grams) is digested for one hour with acetic anhydride (150 gram) and zinc chloride (1 gram), the product is mixed with View Article Online THE REPLACEMENT OF HYDROXYL BY BROMINE. 859 ether, rapidly washed with water, dried over calcium chloride, and fractionated. Almost the whole quantity distils at 258-259' (760 mm.) and consists of pure triacetin, since a second treatment with acetic anhydride and zinc chloride does not alter the properties of the sub- stance. Triacetin (5 grams) was now mixed with the solution of hydrogen bromide in acetic acid (2s gra.ms) and heated in a sealed tube for 10 hours at 150-160", the product was then poured into water and distilled in steam.
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