1-[(E)-3-chloroprop-1-enyl]-4-fluorobenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2E)-3-(4-Fluorophenyl)prop-2-en-1-ol (1.36 g) synthesized in Reference Example 24 was dissolved in dichloromethane (45 mL), pyridine (0.78 g) and thionyl chloride (0.72 mL) were added under ice-cooling, and the mixture was stirred for 30 min. The mixture was diluted with dichloromethane. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane) to give the title compound (1.1 g) as a colorless oil. cooling The organic layer was washed successively with water and saturated brine dried over anhydrous sodium sulfate The solvent was evaporated under reduced pressure the residue was purified by silica gel chromatography (elution solvent; hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a dichloromethane solution (40 mL) of (E)-1-(3-chloroprop-1-en-1-yl)-4-fluorobenzene (2.40 g, 14.0 mmol), rhodium (II) acetate (57.7 mg, 0.140 mmol) was added and then a dichloromethane solution (20 mL) of ethyl diazoacetate (1.92 g, 16.8 mmol) was added dropwise at room temperature over 18 hours with stirring. After completion of the reaction, the reaction solution was concentrated and N,N-dimethylformamide (20 mL), benzylamine (1.50 g, 14.0 mmol), and sodium bicarbonate (1.18 g, 14.0 mmol) were added to the resultant residue and the resultant mixture was stirred at 150° C. for 2 hours. After completion of the reaction, ethyl acetate was added to the reaction solution and the resultant mixture was washed with 1 M hydrochloric acid and a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the obtained residue, ethyl acetate was added and the resultant mixture was filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to obtain the title compound (956 mg, yield 24%). After completion of the reaction the reaction solution was concentrated was added to the reaction solution the resultant mixture was washed with 1 M hydrochloric acid The organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure To the obtained residue, ethyl acetate was added the resultant mixture was filtered The filtrate was concentrated under reduced pressure purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (2E)-3-(4-Fluorophenyl)prop-2-en-1-ol (1.36 g) synthesized in Reference Example 24 was dissolved in dichloromethane (45 mL), pyridine (0.78 g) and thionyl chloride (0.72 mL) were added under ice-cooling, and the mixture was stirred for 30 min. The mixture was diluted with dichloromethane. The organic layer was washed successively with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane) to give the title compound (1.1 g) as a colorless oil. cooling The organic layer was washed successively with water and saturated brine dried over anhydrous sodium sulfate The solvent was evaporated under reduced pressure the residue was purified by silica gel chromatography (elution solvent; hexane)