2,3,5,6-TETRAFLUOROBENZALDEHYDE

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2,3,5,6-tetrafluorobenzaldehyde (25.0 g, 0.14 mol), nitroethane (21.08 g, 0.28 mol), and cyclohexylamine (13.92 g, 0.14 mol) in 150 mL of acetic acid was heated at 80° C. for 5-6 h under an argon atmosphere. After the end of the reaction was established by TLC, the reaction mixture was cooled to room temperature (rt) and the solvent was removed under vacuum. The residue was diluted with water, extracted with ethyl acetate three times. The combined extracts were dried over anhydrous MgSO4, filtered, and concentrated under vacuum. Product was purified by a silica gel chromatography using ethyl acetate and hexanes (1:6 to 1:4) as eluent to afford 30.0 g (91%) of the designed compound as yellow solid. Mass (ESI, positive) m/z 258.0 [M+Na]+. the reaction mixture was cooled to room temperature (rt) the solvent was removed under vacuum The residue was diluted with water extracted with ethyl acetate three times The combined extracts were dried over anhydrous MgSO4 filtered concentrated under vacuum Product was purified by a silica gel chromatography

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2,3,5,6-tetrafluorobenzaldehyde (25.0 g, 0.14 mol), nitroethane (21.08 g, 0.28 mol), and cyclohexylamine (13.92 g, 0.14 mol) in 150 mL of acetic acid was heated at 80° C. for 5-6 h under an argon atmosphere. After the end of the reaction was established by TLC, the reaction mixture was cooled to room temperature (rt) and the solvent was removed under vacuum. The residue was diluted with water, extracted with ethyl acetate three times. The combined extracts were dried over anhydrous MgSO4, filtered, and concentrated under vacuum. Product was purified by a silica gel chromatography using ethyl acetate and hexanes (1:6 to 1:4) as eluent to afford 30.0 g (91%) of the designed compound as yellow solid. Mass (ESI, positive) m/z 258.0 [M+Na]+. the reaction mixture was cooled to room temperature (rt) the solvent was removed under vacuum The residue was diluted with water extracted with ethyl acetate three times The combined extracts were dried over anhydrous MgSO4 filtered concentrated under vacuum Product was purified by a silica gel chromatography

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Into a 500 ml-volume glass-made reactor equipped with a condenser tube, 5.00 g of 2,3,5,6-tetrafluorobenzonitrile, 51.00 g of methanol, 52.00 g of water, 45.00 g of acetic acid and 0.50 g of sponge nickel were charged. After purging the vapor phase moiety with hydrogen gas, the mixed solution was stirred at 60° C. under atmospheric pressure while continuously supplying hydrogen. As the time passed, the reaction solution was sampled and analyzed by means of a gas chromatograph. As a result, it was confirmed that 2,3,5,6-tetrafluorobenzyl alcohol was produced together with 2,3,5,6-tetrafluorobenzaldehyde. The yields in the reaction solution are shown in the table below. Into a 500 ml-volume glass-made reactor equipped with a condenser tube After purging the vapor phase moiety with hydrogen gas the reaction solution was sampled

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2,3,5,6-tetrafluorobenzaldehyde (25.0 g, 0.14 mol), nitroethane (21.08 g, 0.28 mol), and cyclohexylamine (13.92 g, 0.14 mol) in 150 mL of acetic acid was heated at 80° C. for 5-6 h under an argon atmosphere. After the end of the reaction was established by TLC, the reaction mixture was cooled to room temperature (rt) and the solvent was removed under vacuum. The residue was diluted with water, extracted with ethyl acetate three times. The combined extracts were dried over anhydrous MgSO4, filtered, and concentrated under vacuum. Product was purified by a silica gel chromatography using ethyl acetate and hexanes (1:6 to 1:4) as eluent to afford 30.0 g (91%) of the designed compound as yellow solid. Mass (ESI, positive) m/z 258.0 [M+Na]+. the reaction mixture was cooled to room temperature (rt) the solvent was removed under vacuum The residue was diluted with water extracted with ethyl acetate three times The combined extracts were dried over anhydrous MgSO4 filtered concentrated under vacuum Product was purified by a silica gel chromatography