Toxic Fluorine Compounds. IV.¹ ι-Fluoroalkyl Halides

Toxic fluorine compounds. 20. The use of the ω-fluorine atom in the study of the metabolism of branched-chain fatty acids

“…Diethyl 6-fluorohexylmethylmalonate, obtained similarly in 60 % yield from 9 0 g. of 6-fluorohexyl bromide (Pattison & Howell, 1956), had b.p. 89-92°/0.075 mm.…”

“…to complete the formation of the enolate. The mixture was allowed to cool, and 7-fluoroheptyl bromide (Pattison & Howell, 1956) (8-0 g., 40-6 m-moles) was added rapidly with stirring. The mixture was then stirred for 18 hr.…”

“…The heating period in this preparation was 52 hr. The 8-fluoro-octyl chloride was prepared from 1,8-dichloro-octane by the partial fluorination technique (Pattison & Howell, 1956) in 53-2% yield, b.p. 84.5-87.5°/ 9 mm.…”

Toxic fluorine compounds. The use of the ω-fluorine atom in the study of the metabolism of fatty acids containing ethyl, n-propyl and isopropyl branches

“…to a stirred solution of sodium (7.2g., 0-313g.atom) in ethanol (120ml.). The solution was stirred and heated under reflux for a further 30min., and then 5-fluoropentyl bromide (Pattison & Howell, 1956) (35.0g., 02077mole) was run in over lOmin. The resultant mixture was refluxed in an oil bath for 4hr.…”

“…and the solution was stirred until the evolution of hydrogen had ceased (about lhr.). 5-Fluoropentyl bromide (Pattison & Howell, 1956) (25-1g., 0-149mole) was added slowly and the mixture was heated to 850 in an oil bath and kept at that temperature until the pH had become steady at approx. 6-5 (about 43hr.…”