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

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

Procedure: A solution of imidazole-1-carbothioic acid O-[1-(2-bromophenyl)-2,2,2-trifluoroethyl]-ester (Preparation 56, 27.0 g, 73.8 mmol) in toluene (400 ml) was heated at reflux and treated with tri-n-butyltin hydride in three portions: 22 g (75.6 mmol) at first, an additional 10 g (34.4 mmol) after 30 min, and finally 11 g (37.8 mmol) 30 min later. After the addition, the mixture was heated at reflux for another 30 min. The reaction mixture was cooled then the product was distilled at 25 Pa, 60-100° C. to afford the title compound as a colourless oil (17.0 g, 59%). at reflux finally 11 g (37.8 mmol) 30 min After the addition the mixture was heated at reflux for another 30 min The reaction mixture was cooled the product was distilled at 25 Pa, 60-100° C.

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

Procedure: A solution of imidazole-1-carbothioic acid O-[1-(2-bromophenyl)-2,2,2-trifluoroethyl]-ester (Preparation 56, 27.0 g, 73.8 mmol) in toluene (400 ml) was heated at reflux and treated with tri-n-butyltin hydride in three portions: 22 g (75.6 mmol) at first, an additional 10 g (34.4 mmol) after 30 min, and finally 11 g (37.8 mmol) 30 min later. After the addition, the mixture was heated at reflux for another 30 min. The reaction mixture was cooled then the product was distilled at 25 Pa, 60-100° C. to afford the title compound as a colourless oil (17.0 g, 59%). at reflux finally 11 g (37.8 mmol) 30 min After the addition the mixture was heated at reflux for another 30 min The reaction mixture was cooled the product was distilled at 25 Pa, 60-100° C.

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Bromo-2-(2,2,2-trifluoroethyl)benzene (0.5 g) was dissolved in degassed toluene and tributyl(vinyl)tin (0.67 mL), Pd2(dba)3 (0.096 g) and tri-tert-butylphosphine (0.25 mL, 1M solution) were added. Reaction mixture was heated to 40° C. After 4 hours heating was stopped and 1:1 solution of diethyl ether and pentane (10 ml) was added, followed by potassium fluoride (1.0 g). Mixture was stirred for 30 minutes after which it was filtered through a pad of silicagel and the filtrate was concentrated gently at 500 mbar vacuum. The evaporation residue was purified by column chromatography (diethyl ether-pentane) and fractions containing the product were concentrated by house vacuum distillation. The evaporation residue (0.389 g) containing toluene and the desired styrene product was dissolved in dichloromethane (12 mL) and 3-chloroperoxybenzoic acid (0.70 g) was added. Reaction mixture After 4 hours heating was filtered through a pad of silicagel the filtrate was concentrated gently at 500 mbar vacuum The evaporation residue was purified by column chromatography (diethyl ether-pentane) and fractions containing the product were concentrated by house vacuum distillation The evaporation residue (0.389 g) containing toluene the desired styrene product was dissolved in dichloromethane (12 mL) 3-chloroperoxybenzoic acid (0.70 g) was added

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

Procedure: A solution of imidazole-1-carbothioic acid O-[1-(2-bromophenyl)-2,2,2-trifluoroethyl]-ester (Preparation 56, 27.0 g, 73.8 mmol) in toluene (400 ml) was heated at reflux and treated with tri-n-butyltin hydride in three portions: 22 g (75.6 mmol) at first, an additional 10 g (34.4 mmol) after 30 min, and finally 11 g (37.8 mmol) 30 min later. After the addition, the mixture was heated at reflux for another 30 min. The reaction mixture was cooled then the product was distilled at 25 Pa, 60-100° C. to afford the title compound as a colourless oil (17.0 g, 59%). at reflux finally 11 g (37.8 mmol) 30 min After the addition the mixture was heated at reflux for another 30 min The reaction mixture was cooled the product was distilled at 25 Pa, 60-100° C.