1-chloro-2-ethyl-3-fluorobenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution (120 mL) of 1-chloro-3-fluoro-2-vinylbenzene (9.45 g) in ethyl acetate were added sodium acetate (4.92 g) and 10% Pd/C (50% water-containing product, 0.95 g), and the mixture was vigorously stirred under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated. The residue was partitioned with ethyl acetate-water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound as a colorless oil (yield: 8.4 g). The catalyst was filtered off the filtrate was concentrated The residue was partitioned with ethyl acetate-water The organic layer was washed with saturated brine dried over anhydrous sodium sulfate concentrated

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-chloro-2-ethyl-3-fluorobenzene (8.0 g) and anhydrous aluminum chloride (13.09 g) was stirred at 40° C., acetyl chloride (3 drops) was added thereto, and the mixture was stirred for 10 min. The mixture was cooled to room temperature, acetyl chloride (3.9 g) was added to the mixture, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into ice water, and 2 mol/L hydrochloric acid was added thereto. The mixture was extracted with methylene chloride (240 mL), washed with water, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate) to give the title compound as a colorless oil (yield: 3.84 g). the mixture was stirred for 10 min The mixture was cooled to room temperature the mixture was stirred at room temperature for 2 hr was added The mixture was extracted with methylene chloride (240 mL) washed with water dried over anhydrous sodium sulfate concentrated The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate)