Hydrochloric Acid → HCID 178447921, compound

Participants

Reaction Steps

A mixture of 5.0 g (13.1 mmol) of 4-propylcyclohexyl-3-chloro-5-fluoro-4-iodobenzene [prepared by the same method as in the second step of Example 1 with the exception that 4-propylcyclohexyl-3-chloro-5-fluorobenzene was used in place of the 4-propoxycyclohexyl-3-chloro-5-fluorobenzene used in the second step of Example 1], 3.1 g (19.7 mmol) of dihydroxy(3,4-difluorophenyl)borane [prepared by reacting a Grignard reagent, which was prepared in turn from 3,4-difluorobromobenzene, with trimethoxyborane, and then hydrolyzing with hydrochloric acid], 3.6 g (26.3 mmol) of potassium carbonate, 0.5 g of 5% Pd-C, and 50 ml of mixed solvent of toluene/ethanol/water (1/1/1) was heated to reflux for 32 hours. After the catalyst was removed by filtration, the mixture was extracted with 100 ml of toluene. The organic layer thus obtained was washed with water thrice and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduce pressure and the residue thus obtained was subjected to silica gel column chromatography (eluent: heptane) to obtain 4.4 g of a crude 4′-(trans-4-propyl-cyclohexyl)-2′-chloro-3,4,6′-trifluorobiphenyl. This product was recrystallized from a mixed solvent of ethanol/ethyl acetate to obtain 0.9 g of the subject compound. (Yield: 18.3%)

Provenance & Evidence