Diethylene Glycol → 4-Ethyl-2-fluoro-1,1'-biphenyl

Participants

Reaction Steps

4-Acetyl-2-fluorobiphenyl (150 gram), 99% hydrazine hydrate (150 ml), potassium hydroxide (105 gram), digol (900 ml) and xylene (150 ml) were heated at 125° C. for 16 hours with stirring, after which the xylene and excess hydrazine hydrate were distilled until the internal temperature reached 165° C. The mixture was heated under reflux for three hours, cooled to 40° and poured into 5 liters of water. The product was extracted with petroleum ether (bp 60°-80°, 2×2 liter), the extract washed with water, dried over anhydrous sodium sulphate and evaporated. 4-Ethyl-2-fluorobiphenyl (95 gram, 68% theory) formed a colourless oil bp 130°/0.8 mm. Other 4-Alkyl-2-fluorobiphenyls were prepared by reaction of 2-fluoro-4-biphenylyl magnesium bromides with n-alkyl bromides and were colourless oils with the following properties listed in Table 5.

Provenance & Evidence