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37.1.1.7.3 Method 3: Addition of Organometallic Reagents

DOI: 10.1055/sos-SD-037-00003

Van Orden, L. J.; Jasti, R.; Rychnovsky, S. D.Science of Synthesis, (20083743.

Due to donation from the lone-pair electrons on oxygen, the carbonhalogen bond of an α-halo ether is very susceptible toward nucleophilic attack. Organocuprates and Grignard reagents serve as good coupling partners for α-chloro ethers 163 and 165 to give branched chloroalkyl ether 164 and methoxyacetonitrile (166), respectively (Scheme 56).[‌98‌,‌99‌] Notably, the alkyl Grignard reagent selectively cleaves only the more reactive CCl bond and the secondary chlorine atom is maintained.

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