1-methoxy-2-(2,2,2-trifluoroethoxy)benzene

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 of 1-methoxy-2-(2,2,2-trifluoroethoxy)benzene (3.83 g) in dry methylene chloride (50 ml) was added boron tribromide (3.1 ml) with stirring under ice cooling, and the mixture was reacted for 30 minutes. The reaction mixture was poured into an aqueous sodium bicarbonate solution (500 ml), and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (20/1) as eluent to give 2.37 g of 2-(2,2,2-trifluoroethoxy)phenol melting at 49°-50° C. the mixture was reacted for 30 minutes the mixture was extracted with diethyl ether The extract was washed with water dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (20/1) as eluent

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

Procedure: To a solution of 1-methoxy-2-(2,2,2-trifluoroethoxy)benzene (3.83 g) in dry methylene chloride (50 ml) was added boron tribromide (3.1 ml) with stirring under ice cooling, and the mixture was reacted for 30 minutes. The reaction mixture was poured into an aqueous sodium bicarbonate solution (500 ml), and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (20/1) as eluent to give 2.37 g of 2-(2,2,2-trifluoroethoxy)phenol melting at 49°-50° C. the mixture was reacted for 30 minutes the mixture was extracted with diethyl ether The extract was washed with water dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (20/1) as eluent

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To dry N,N-dimethylformamide (10 ml) were added 2-methoxyphenol (150 mg), 2,2,2-trifluoroethyl iodide (584 mg) and potassium carbonate (400 mg), and the mixture was stirred vigorously at 130° C. for 6 hours. To the reaction mixture was added water, and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and chloroform (5/2) as eluent to give 179 mg of 1-methoxy-2-(2,2,2-trifluoroethoxy) benzene as an oil. the mixture was extracted with diethyl ether The extract was washed with water dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and chloroform (5/2) as eluent

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To dry N,N-dimethylformamide (10 ml) were added 2-methoxyphenol (150 mg), 2,2,2-trifluoroethyl iodide (584 mg) and potassium carbonate (400 mg), and the mixture was stirred vigorously at 130° C. for 6 hours. To the reaction mixture was added water, and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and chloroform (5/2) as eluent to give 179 mg of 1-methoxy-2-(2,2,2-trifluoroethoxy) benzene as an oil. the mixture was extracted with diethyl ether The extract was washed with water dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and chloroform (5/2) as eluent

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

Procedure: To a solution of 1-methoxy-2-(2,2,2-trifluoroethoxy)benzene (3.83 g) in dry methylene chloride (50 ml) was added boron tribromide (3.1 ml) with stirring under ice cooling, and the mixture was reacted for 30 minutes. The reaction mixture was poured into an aqueous sodium bicarbonate solution (500 ml), and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (20/1) as eluent to give 2.37 g of 2-(2,2,2-trifluoroethoxy)phenol melting at 49°-50° C. the mixture was reacted for 30 minutes the mixture was extracted with diethyl ether The extract was washed with water dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (20/1) as eluent

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To dry N,N-dimethylformamide (10 ml) were added 2-methoxyphenol (150 mg), 2,2,2-trifluoroethyl iodide (584 mg) and potassium carbonate (400 mg), and the mixture was stirred vigorously at 130° C. for 6 hours. To the reaction mixture was added water, and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and chloroform (5/2) as eluent to give 179 mg of 1-methoxy-2-(2,2,2-trifluoroethoxy) benzene as an oil. the mixture was extracted with diethyl ether The extract was washed with water dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and chloroform (5/2) as eluent

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

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

Procedure: Boron tribromide (2.8 ml, 0.03 mole) was added to a solution of 1-methoxy-2-(2,2,2-trifluoroethoxy)benzene (X) (6.0 g, 0.03 mole) in methylene chloride (90 ml) with stirring below −10° C. Reaction was stirred at −10 to −20° C. for 30 minutes. The reaction mixture was quenched using aqueous sodium bicarbonate solution. Organic layer was separated, washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure to give 4.0 g of (XI) as oil. Purity (by GC)=95%. Reaction was stirred at −10 to −20° C. for 30 minutes The reaction mixture was quenched Organic layer was separated washed with water dried over sodium sulphate The solvent was evaporated under reduced pressure

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-Methoxy phenol (IX) (5 g, 0.04 moles) in N-methylpyrrolidone (50 ml) were added, potassium carbonate (7.8 g, 0.06 mole) and 2,2,2-trifluoroethyl iodide (33.8 g, 0.16 mole) under stirring. The reaction mixture was stirred vigorously at 120° C. for 10 hours. Water (150 ml) was added to the reaction mixture and the mixture was extracted in Toluene (250 ml). Organic layer was washed with 1 N Sodium hydroxide solution (150 ml), followed by brine wash. The extract was dried over sodium sulphate. The solvent was evaporated under reduced pressure to give 7.2 g of (X) as oil. Purity (by GC)=94% the mixture was extracted in Toluene (250 ml) Organic layer was washed with 1 N Sodium hydroxide solution (150 ml) wash The extract was dried over sodium sulphate The solvent was evaporated under reduced pressure

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

Procedure: To a solution of 1-methoxy-2-(2,2,2-trifluoroethoxy)benzene (3.83 g) in dry methylene chloride (50 ml) was added boron tribromide (3.1 ml) with stirring under ice cooling, and the mixture was reacted for 30 minutes. The reaction mixture was poured into an aqueous sodium bicarbonate solution (500 ml), and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (20/1) as eluent to give 2.37 g of 2-(2,2,2-trifluoroethoxy)phenol melting at 49°-50° C. the mixture was reacted for 30 minutes the mixture was extracted with diethyl ether The extract was washed with water dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and diethyl ether (20/1) as eluent

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To dry N,N-dimethylformamide (10 ml) were added 2-methoxyphenol (150 mg), 2,2,2-trifluoroethyl iodide (584 mg) and potassium carbonate (400 mg), and the mixture was stirred vigorously at 130° C. for 6 hours. To the reaction mixture was added water, and the mixture was extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and chloroform (5/2) as eluent to give 179 mg of 1-methoxy-2-(2,2,2-trifluoroethoxy) benzene as an oil. the mixture was extracted with diethyl ether The extract was washed with water dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of hexane and chloroform (5/2) as eluent