Chlorohydrins ethylene bromohydrin

In this work on compounds containing the C—F link, it was obviously desirable to prepare 2-fluoroethanol, both for toxicity tests on the compound itself, and as a starting material for the production of other fluorine compounds. Swarts1 was unable to obtain 2-fluoroethanol by the action of silver fluoride or mercuric fluoride on either ethylene chlorohydrin or ethylene bromohydrin. He obtained acetaldehyde in each case. He ultimately obtained fluoroethanol in very poor yield by the indirect method of hydrolysing fluoroacetin (from bromoacetin and mercuric fluoride) for 80 hr. with dilute mineral acid. 

Ethyl 2-cyano-3-ethoxyacrylate, el32 A-Ethyldiisopropylamine, d418 Ethylene bromohydrin, b279 Ethylene chlorohydrin, cl03 Ethylene cyanohydrin, hl69 Ethylene diacetate, el7... 

Ethylene chloride is not isolated directly since an azeotrope (b.p. 97.8°) of the chlorohydrin (42.5 %) and water distils from the reaction mixture. Instead, calcium hydroxide is added, the resulting alkaline medium causing formation of ethylene oxide (b.p. 10.7°) which can be easily separated. This is then led, together with the equivalent amount of HC1, into preformed ethylene chlorohydrin, whereupon ethylene chlorohydrin (b.p. 128.7°/760 mm) is formed quantitatively. For a synthesis of ethylene bromohydrin see McDowell.270... 

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