Reactions of Organozinc Reagents with Acid Chlorides

3 Reactions of Organozinc Reagents with Acid Chlorides 

It is clear from the preceding chapter that the oxidative addition of Rieke zinc is general and can be used with most any organic halide. The reaction proceeds with alkyl iodides, bromides and even most chlorides. Significantly, the reaction proceeds with aryl iodides, bromides, and even some chlorides. Most unusual of all, the reaction proceeds with vinyl iodides and bromides. Moreover, the yields are always in the range of90-95%. In all cases, the molecules can contain 

Typical Generation of Organozinc Halides from Organic Halides and Active Zinc and Their Copper-Mediated Coupling with Acid Chlorides 

The resultant crude product was chromatographed on flash silica gel using gradient elution (hexanes to remove naphthalene first, then hexanes/ethyl acetate) to give ethyh4-(l-oxopentyl)benzoate (1.360g, 5.81 mmol) as a white crystalline solid in 83% isolated yield mp 47.5-48.0°C. 

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