Displacement reactions specialized procedures

The procedure for 1-ethoxy-1-phenylethene is an illustration of a general synthetic method for 1-substituted vinyl ethers, which are not accessible via 1-metalla-tion [9] (compare Chap. IV, Exp. 1). The synthesis starts with the reaction of a Grignard compound with a 1,2-dibromoalkyl ether [231]. A halogen atom in the 1-position of an ether group is very readily replacable, even under non-polar conditions. This reaction is a special case of nucleophilic displacement in which the... 

If 44 reacts with benzyl bromide, the product is AT-benzylphthalimide (45) via a straightforward Sn2 displacement. To generate the amine, the imide can be hydrolyzed by acid-base reactions (1. aqueous base 2. aqueous acid) to give the amine (46) and phthalic acid (47). The reaction of 45 with aqueous hydroxide is an example of an acyl substitution reaction that will be introduced in Chapter 16 (Section 16.8). For several reasons, it will not be discussed at this time. A better procedure has been developed that treats 45 with hydrazine (NH2NH2) to generate amine 46 and a molecule known as a hydrazide, 48. Hydrazide 48 is easily separated from amine 46. A hydrazide is one of those specialized chemicals encountered from time to time, but not discussed in detail. 

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