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An efficient and inexpensive method for the substitution of allylic hydroxyl group with fluoride, without allylic rearrangement, and elimination was developed. This method consists of treating an allylic alcohol with methyllithium, followed by p-toluene sulfonyl fluoride, lithium fluoride and 12-Crown-4. This methodology was proved to be efficient by preparing geranyl fluoride, neryl fluoride, cinnamyl fluoride, E,E-farnesyl fluoride, retinyl fluoride and 4-fluoro-2-methyl-6-(p-tolyl)-2-heptene.
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