Butyl bromide preparation from 1-butanol

The preparation of -butyl bromide as an example of ester formation by Method 1 (p. 95) has certain advantages over the above preparation of ethyl bromide. -Butanol is free from Excise restrictions, and the -butyl bromide is of course less volatile. and therefore more readily manipulated without loss than ethyl bromide furthermore, the n-butyl bromide boils ca. 40° below -butyl ether, and traces of the latter formed in the reaction can therefore be readily eliminated by fractional distillation. 

Reaction with alcohols and phenols. Horner and co-workers introduced use of the reagents for the preparation of alkyl and aryl halides from alcohols or phenols, and Wiley and co-workers established that the reagents have considerable advantage over phosphorus pentahalides in the C—OH—C—X conversion and discussed the mechanism. For the preparation of n-butyl bromide the Wiley group added bromine under nitrogen to a solution of n-butanol and triphenylphosphine in dimethyl-formamide until 2 drops persisted in giving the solution an orange tint. Volatile... 

A soln. of n-butyl benzoylformate in anhydrous ether added to a soln. of 2 moles bromomagnesium n-butoxide prepared from ethylmagnesium bromide and n-butanol in ether refluxed 3 hrs. n-butyl mandelate. Y 96%. F. e. and limitations s. 1.1. Lapkin and N. A. Karavanov, 7K. 30, 2677 (1960) C. A. 55, 14361e. 

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