4-(2,2,2-trifluoroethyl)phenol

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:0.00; pressure:0.00; stir:

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-(2,2,2-trifluoroethyl)phenol (1.00 g, 5.68 mmol) in CH2Cl2 (5.0 ml) was added trifluoromethanesulfonic acid (0.0151 ml, 0.170 mmol) with stirring. A solution of acetic chloride (0.444 ml, 6.25 mmol) in CH2Cl2 (5.0 ml) was added drop wise to the reaction. After stirred 45 min at RT, all the phenol was consumed. The product mixture was diluted with CH2Cl2, washed with saturated sodium bicarbonate. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dried in vacuum until no weight loss was observed. To the above residue was added anhydrous aluminum(III) chloride (0.757 g, 5.68 mmol). The mixture was heated at 150° C. for 1 h until all the starting material was consumed (monitored by TLC). The resulted brown gum was cooled to 0° C., diluted with diethyl ether and 1N HCl. Layers were separated. The aqueous layer was extracted with ether. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column (2-15% EtOAc/hexane) to afford the title compound. wise to the reaction After stirred 45 min at RT all the phenol was consumed The product mixture was diluted with CH2Cl2 washed with saturated sodium bicarbonate The organic layer was dried over Na2SO4 filtered concentrated The residue was dried in vacuum until no weight loss was consumed (monitored by TLC) The resulted brown gum was cooled to 0° C. diluted with diethyl ether and 1N HCl Layers were separated The aqueous layer was extracted with ether dried over Na2SO4 filtered concentrated The residue was purified on silica gel column (2-15% EtOAc/hexane)

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-(2,2,2-trifluoroethyl)phenol (1.00 g, 5.68 mmol) in CH2Cl2 (5.0 ml) was added trifluoromethanesulfonic acid (0.0151 ml, 0.170 mmol) with stirring. A solution of acetic chloride (0.444 ml, 6.25 mmol) in CH2Cl2 (5.0 ml) was added drop wise to the reaction. After stirred 45 min at RT, all the phenol was consumed. The product mixture was diluted with CH2Cl2, washed with saturated sodium bicarbonate. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dried in vacuum until no weight loss was observed. To the above residue was added anhydrous aluminum(III) chloride (0.757 g, 5.68 mmol). The mixture was heated at 150° C. for 1 h until all the starting material was consumed (monitored by TLC). The resulted brown gum was cooled to 0° C., diluted with diethyl ether and 1N HCl. Layers were separated. The aqueous layer was extracted with ether. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column (2-15% EtOAc/hexane) to afford the title compound. wise to the reaction After stirred 45 min at RT all the phenol was consumed The product mixture was diluted with CH2Cl2 washed with saturated sodium bicarbonate The organic layer was dried over Na2SO4 filtered concentrated The residue was dried in vacuum until no weight loss was consumed (monitored by TLC) The resulted brown gum was cooled to 0° C. diluted with diethyl ether and 1N HCl Layers were separated The aqueous layer was extracted with ether dried over Na2SO4 filtered concentrated The residue was purified on silica gel column (2-15% EtOAc/hexane)

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

実験手順: To a solution of 4-(1-chloro-2,2,2-trifluoroethyl)phenol (3.60 g, 17.1 mmol) in THF was added sodium borohydride (0.903 ml, 25.6 mmol) in one portion. The reaction was stirred at RT for 18 h, and then quenched with MeOH. The resulting mixture was concentrated and diluted with EtOAc. After washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dried in vacuum to afford 4-(2,2,2-trifluoroethyl)phenol as a colorless oil. MS m/z: 175(M−1). quenched with MeOH The resulting mixture was concentrated diluted with EtOAc After washed with water and brine The organic layer was dried over Na2SO4 filtered concentrated The residue was dried in vacuum

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

実験手順: To a solution of 4-(1-chloro-2,2,2-trifluoroethyl)phenol (3.60 g, 17.1 mmol) in THF was added sodium borohydride (0.903 ml, 25.6 mmol) in one portion. The reaction was stirred at RT for 18 h, and then quenched with MeOH. The resulting mixture was concentrated and diluted with EtOAc. After washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dried in vacuum to afford 4-(2,2,2-trifluoroethyl)phenol as a colorless oil. MS m/z: 175(M−1). quenched with MeOH The resulting mixture was concentrated diluted with EtOAc After washed with water and brine The organic layer was dried over Na2SO4 filtered concentrated The residue was dried in vacuum

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

実験手順: To a solution of 4-(1-chloro-2,2,2-trifluoroethyl)phenol (3.60 g, 17.1 mmol) in THF was added sodium borohydride (0.903 ml, 25.6 mmol) in one portion. The reaction was stirred at RT for 18 h, and then quenched with MeOH. The resulting mixture was concentrated and diluted with EtOAc. After washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dried in vacuum to afford 4-(2,2,2-trifluoroethyl)phenol as a colorless oil. MS m/z: 175(M−1). quenched with MeOH The resulting mixture was concentrated diluted with EtOAc After washed with water and brine The organic layer was dried over Na2SO4 filtered concentrated The residue was dried in vacuum

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-(2,2,2-trifluoroethyl)phenol (1.00 g, 5.68 mmol) in CH2Cl2 (5.0 ml) was added trifluoromethanesulfonic acid (0.0151 ml, 0.170 mmol) with stirring. A solution of acetic chloride (0.444 ml, 6.25 mmol) in CH2Cl2 (5.0 ml) was added drop wise to the reaction. After stirred 45 min at RT, all the phenol was consumed. The product mixture was diluted with CH2Cl2, washed with saturated sodium bicarbonate. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dried in vacuum until no weight loss was observed. To the above residue was added anhydrous aluminum(III) chloride (0.757 g, 5.68 mmol). The mixture was heated at 150° C. for 1 h until all the starting material was consumed (monitored by TLC). The resulted brown gum was cooled to 0° C., diluted with diethyl ether and 1N HCl. Layers were separated. The aqueous layer was extracted with ether. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column (2-15% EtOAc/hexane) to afford the title compound. wise to the reaction After stirred 45 min at RT all the phenol was consumed The product mixture was diluted with CH2Cl2 washed with saturated sodium bicarbonate The organic layer was dried over Na2SO4 filtered concentrated The residue was dried in vacuum until no weight loss was consumed (monitored by TLC) The resulted brown gum was cooled to 0° C. diluted with diethyl ether and 1N HCl Layers were separated The aqueous layer was extracted with ether dried over Na2SO4 filtered concentrated The residue was purified on silica gel column (2-15% EtOAc/hexane)

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

実験手順: To a solution of 4-(1-chloro-2,2,2-trifluoroethyl)phenol (3.60 g, 17.1 mmol) in THF was added sodium borohydride (0.903 ml, 25.6 mmol) in one portion. The reaction was stirred at RT for 18 h, and then quenched with MeOH. The resulting mixture was concentrated and diluted with EtOAc. After washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dried in vacuum to afford 4-(2,2,2-trifluoroethyl)phenol as a colorless oil. MS m/z: 175(M−1). quenched with MeOH The resulting mixture was concentrated diluted with EtOAc After washed with water and brine The organic layer was dried over Na2SO4 filtered concentrated The residue was dried in vacuum

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

実験手順: To a solution of 4-(1-chloro-2,2,2-trifluoroethyl)phenol (3.60 g, 17.1 mmol) in THF was added sodium borohydride (0.903 ml, 25.6 mmol) in one portion. The reaction was stirred at RT for 18 h, and then quenched with MeOH. The resulting mixture was concentrated and diluted with EtOAc. After washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dried in vacuum to afford 4-(2,2,2-trifluoroethyl)phenol as a colorless oil. MS m/z: 175(M−1). quenched with MeOH The resulting mixture was concentrated diluted with EtOAc After washed with water and brine The organic layer was dried over Na2SO4 filtered concentrated The residue was dried in vacuum