1-bromo-3-(2,2,2-trifluoroethoxy)benzene

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (3 g, 11.81 mmol) in dimethylformamide (20 mL) was added 3-bromophenol (1 g, 5.78 mmol) and NaOH (500 mg, 12.50 mmol). The resulting solution was stirred at 100° C. for 3 h. The reaction mixture was quenched by the adding H2O (100 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried (Na2SO4) and concentrated, and the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether) to provide 1.1 g (31%) of 1-bromo-3-(2,2,2-trifluoroethoxy)benzene. The reaction mixture was quenched by the adding H2O (100 mL) extracted with methylene chloride (3×50 mL) The combined organic layers were dried (Na2SO4) concentrated the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (3 g, 11.81 mmol) in dimethylformamide (20 mL) was added 3-bromophenol (1 g, 5.78 mmol) and NaOH (500 mg, 12.50 mmol). The resulting solution was stirred at 100° C. for 3 h. The reaction mixture was quenched by the adding H2O (100 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried (Na2SO4) and concentrated, and the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether) to provide 1.1 g (31%) of 1-bromo-3-(2,2,2-trifluoroethoxy)benzene. The reaction mixture was quenched by the adding H2O (100 mL) extracted with methylene chloride (3×50 mL) The combined organic layers were dried (Na2SO4) concentrated the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether)

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (3 g, 11.81 mmol) in dimethylformamide (20 mL) was added 3-bromophenol (1 g, 5.78 mmol) and NaOH (500 mg, 12.50 mmol). The resulting solution was stirred at 100° C. for 3 h. The reaction mixture was quenched by the adding H2O (100 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried (Na2SO4) and concentrated, and the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether) to provide 1.1 g (31%) of 1-bromo-3-(2,2,2-trifluoroethoxy)benzene. The reaction mixture was quenched by the adding H2O (100 mL) extracted with methylene chloride (3×50 mL) The combined organic layers were dried (Na2SO4) concentrated the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (3 g, 11.81 mmol) in dimethylformamide (20 mL) was added 3-bromophenol (1 g, 5.78 mmol) and NaOH (500 mg, 12.50 mmol). The resulting solution was stirred at 100° C. for 3 h. The reaction mixture was quenched by the adding H2O (100 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried (Na2SO4) and concentrated, and the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether) to provide 1.1 g (31%) of 1-bromo-3-(2,2,2-trifluoroethoxy)benzene. The reaction mixture was quenched by the adding H2O (100 mL) extracted with methylene chloride (3×50 mL) The combined organic layers were dried (Na2SO4) concentrated the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (3 g, 11.81 mmol) in dimethylformamide (20 mL) was added 3-bromophenol (1 g, 5.78 mmol) and NaOH (500 mg, 12.50 mmol). The resulting solution was stirred at 100° C. for 3 h. The reaction mixture was quenched by the adding H2O (100 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried (Na2SO4) and concentrated, and the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether) to provide 1.1 g (31%) of 1-bromo-3-(2,2,2-trifluoroethoxy)benzene. The reaction mixture was quenched by the adding H2O (100 mL) extracted with methylene chloride (3×50 mL) The combined organic layers were dried (Na2SO4) concentrated the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (3 g, 11.81 mmol) in dimethylformamide (20 mL) was added 3-bromophenol (1 g, 5.78 mmol) and NaOH (500 mg, 12.50 mmol). The resulting solution was stirred at 100° C. for 3 h. The reaction mixture was quenched by the adding H2O (100 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried (Na2SO4) and concentrated, and the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether) to provide 1.1 g (31%) of 1-bromo-3-(2,2,2-trifluoroethoxy)benzene. The reaction mixture was quenched by the adding H2O (100 mL) extracted with methylene chloride (3×50 mL) The combined organic layers were dried (Na2SO4) concentrated the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether)