4-bromo-2-fluoro-1-(2,2,2-trifluoroethyl)benzene

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

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

Procedure: A solution of 6.78 g (23.7 mmol, purity 90%) of the compound from Example 74A in toluene (339 ml) was admixed under argon at RT with 7.74 g (35.6 mmol) of the compound from Example 29A in ethanol (112 ml) and 3.61 g (26.1 mmol) of potassium carbonate. After stirring for 10 min, 2.74 g (2.37 mmol) of tetrakis(triphenylphosphine)palladium and then 4.14 g (71.2 mmol) of potassium fluoride in water (71 ml) were added. The mixture was stirred under reflux for 8 h, and the reaction solution was cooled and diluted with ethyl acetate. The reaction solution was washed in water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by means of column chromatography (silica gel, dichloromethane, dichloromethane/methanol 150:1→100:1). The product fractions were concentrated under reduced pressure and the solid obtained was purified by stirring with diethyl ether. Yield: 6.00 g (50% of theory, purity 62%) The mixture was stirred under reflux for 8 h the reaction solution was cooled The reaction solution was washed in water the organic phase was dried over magnesium sulphate filtered concentrated under reduced pressure The residue was purified by means of column chromatography (silica gel, dichloromethane, dichloromethane/methanol 150:1→100:1) The product fractions were concentrated under reduced pressure the solid obtained was purified by stirring with diethyl ether

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

Procedure: A solution of 6.78 g (23.7 mmol, purity 90%) of the compound from Example 74A in toluene (339 ml) was admixed under argon at RT with 7.74 g (35.6 mmol) of the compound from Example 29A in ethanol (112 ml) and 3.61 g (26.1 mmol) of potassium carbonate. After stirring for 10 min, 2.74 g (2.37 mmol) of tetrakis(triphenylphosphine)palladium and then 4.14 g (71.2 mmol) of potassium fluoride in water (71 ml) were added. The mixture was stirred under reflux for 8 h, and the reaction solution was cooled and diluted with ethyl acetate. The reaction solution was washed in water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by means of column chromatography (silica gel, dichloromethane, dichloromethane/methanol 150:1→100:1). The product fractions were concentrated under reduced pressure and the solid obtained was purified by stirring with diethyl ether. Yield: 6.00 g (50% of theory, purity 62%) The mixture was stirred under reflux for 8 h the reaction solution was cooled The reaction solution was washed in water the organic phase was dried over magnesium sulphate filtered concentrated under reduced pressure The residue was purified by means of column chromatography (silica gel, dichloromethane, dichloromethane/methanol 150:1→100:1) The product fractions were concentrated under reduced pressure the solid obtained was purified by stirring with diethyl ether

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

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

Procedure: A solution of 6.78 g (23.7 mmol, purity 90%) of the compound from Example 74A in toluene (339 ml) was admixed under argon at RT with 7.74 g (35.6 mmol) of the compound from Example 29A in ethanol (112 ml) and 3.61 g (26.1 mmol) of potassium carbonate. After stirring for 10 min, 2.74 g (2.37 mmol) of tetrakis(triphenylphosphine)palladium and then 4.14 g (71.2 mmol) of potassium fluoride in water (71 ml) were added. The mixture was stirred under reflux for 8 h, and the reaction solution was cooled and diluted with ethyl acetate. The reaction solution was washed in water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by means of column chromatography (silica gel, dichloromethane, dichloromethane/methanol 150:1→100:1). The product fractions were concentrated under reduced pressure and the solid obtained was purified by stirring with diethyl ether. Yield: 6.00 g (50% of theory, purity 62%) The mixture was stirred under reflux for 8 h the reaction solution was cooled The reaction solution was washed in water the organic phase was dried over magnesium sulphate filtered concentrated under reduced pressure The residue was purified by means of column chromatography (silica gel, dichloromethane, dichloromethane/methanol 150:1→100:1) The product fractions were concentrated under reduced pressure the solid obtained was purified by stirring with diethyl ether