Fluoroethanol preparation

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. 

In Report no. 3 on fluoroacetates and allied compounds to the Ministry of Supply2 we described a very simple and efficient preparation of fluoroethanol (F.E.A.) by heating together ethylene chlorohydrin and potassium fluoride in a rotating autoclave at 135° for 4 hr.3... 

In view of the fact that fluoroethanol is as toxic as methyl fluoroacetate (or as fluoroacetic acid), it seemed worth while preparing a compound in which the active parts of these molecules were combined, in the hope of obtaining a compound of increased potency. Such a compound is 2-fluoroethyl fluoroacetate, first prepared and described by us in 1943.1 This ester was readily prepared by the action of fluoroacetyl chloride on fluoroethanol. It is a stable, mobile liquid possessing an extremely faint odour. 

Fluoroethyl aminoacetate hydrochloride (XIII) was readily prepared by esterifying glycine with fluoroethanol (F.E.A.) according to the Fischer-Speier method ... 

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