Benzene, 1-(chloromethyl)-2-fluoro- → HCID 20364964, compound

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Reaction Steps

By the method of Example 43, 2-chloromethyl-5-hydroxy-1,3-dioxane was reacted with sodium hydride and o-fluorobenzyl chloride to yield 2-chloromethyl-5-(2-fluorobenzyloxy)-1,3-dioxane. This mixture of isomers was distilled using a short path distillation apparatus at 0.1 mm to obtain three fractions. Fraction 1, b.p. 95°-100°/0.1 mm was found by VPC analysis to be 3.8% cis-2-chloromethyl-5-(2-fluorobenzyloxy)-1,3-dioxane (the remainder in each case being the trans isomer). Fraction 2, b.p. 98°-102°/0.1 mm was 13.8% cis isomer. Fraction 3, b.p. 165°-170°/0.1 mm was 99% cis and solidified on standing; the solid was sublimed to a solid, m.p. 60°-62°, which was found by nmr analysis to 94% cis isomer and 6% trans isomer.

Provenance & Evidence