Process for forming a fluoromethyl ketone

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

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530330, 530331, 530335, 560 37, 560 51, 560169, 560170, 560174, 560192, 568319, 568355, 568397, C07C31504, C07C 4541

Patent

active

052102726

ABSTRACT:
The preparation of magnesium benzyl fluoromalonate and other equivalent materials, the synthetic equivalents of the --CH.sub.2 F moiety, is described. Reaction between these reagents and the in situ-formed imidazolides of various carboxylic acids gives beta-keto-alpha-fluoroesters, which upon hydrogenation and spontaneous decarboxylation yields fluoromethyl ketones in excellent yields. The overall transformation from RCOOH to RCOCH.sub.2 F is thus illustrated.

REFERENCES:
patent: 4518528 (1985-05-01), Rasnick
Rozen, S. et al., Tetrahedron Letters, 41:1111-1153, (1985).
Brooks, D. W. et al., Angew. Chem. Int. Ed. Eng., 18:72-74, (1979).
Mansour, T. S., Synth. Commun., 19 (Nos. 3 & 4): 659-665, (1989).

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