1-chloro-2-(trifluoromethyl)benzene

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

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

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

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: BuLi (1.6 M in hexane, 173 mL, 277 mmol) was added to a sol. of 2-trifluoromethyl-chlorobenzene (50.0 g, 277 mmol) in THF (500 mL) at −70° C. The sol. was stirred for 2 h at −70° C., and DMF (21.3 mL, 277 mmol) in THF (100 mL) was added. The mixture was allowed to warm to rt overnight. Water was added (200 mL), and the mixture was extracted with Et2O (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane/EtOAc 20:1) yielded the title compound (37.4 g, 65%). LC-MS: tR=0.96 min. to warm to rt overnight the mixture was extracted with Et2O (2×) extracts were dried over MgSO4 filtered the solvents were removed under reduced pressure Purification of the residue by FC (heptane/EtOAc 20:1)

Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: BuLi (1.6 M in hexane, 173 mL, 277 mmol) was added to a sol. of 2-trifluoromethyl-chlorobenzene (50.0 g, 277 mmol) in THF (500 mL) at −70° C. The sol. was stirred for 2 h at −70° C., and DMF (21.3 mL, 277 mmol) in THF (100 mL) was added. The mixture was allowed to warm to rt overnight. Water was added (200 mL), and the mixture was extracted with Et2O (2×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (heptane/EtOAc 20:1) yielded the title compound (37.4 g, 65%). LC-MS: tR=0.96 min. to warm to rt overnight the mixture was extracted with Et2O (2×) extracts were dried over MgSO4 filtered the solvents were removed under reduced pressure Purification of the residue by FC (heptane/EtOAc 20:1)

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

Procedure: A solution of 0.6 mole of 2-chlorotrifluoromethylbenzene in 1 l of tetrahydrofuran is cooled to -65° C. and 0.58 mole of butyllithium dissolved in hexane is added. The mixture is maintained at the same temperature for 2 hours and a mixture containing 44 ml of dimethylformamide and 200 ml of tetrahydrofuran is then added dropwise. The reaction medium is allowed to return to ambient temperature, 600 ml of water are added, extraction is then carried out with ethyl ether followed by evaporation to dryness. The product is distilled to purify. is added The mixture is maintained at the same temperature for 2 hours is then added dropwise to return to ambient temperature extraction followed by evaporation to dryness The product is distilled to purify

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

Procedure: A solution of 0.6 mole of 2-chlorotrifluoromethylbenzene in 1 l of tetrahydrofuran is cooled to -65° C. and 0.58 mole of butyllithium dissolved in hexane is added. The mixture is maintained at the same temperature for 2 hours and a mixture containing 44 ml of dimethylformamide and 200 ml of tetrahydrofuran is then added dropwise. The reaction medium is allowed to return to ambient temperature, 600 ml of water are added, extraction is then carried out with ethyl ether followed by evaporation to dryness. The product is distilled to purify. is added The mixture is maintained at the same temperature for 2 hours is then added dropwise to return to ambient temperature extraction followed by evaporation to dryness The product is distilled to purify

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

Procedure: In an autoclave made of a metal were placed 45.13 g of ortho-chlorobenzotrifluoride, 6.8 g of paraisopropylphenol, 88.5 mg of palladium chloride, 213 mg of 1,4-bisdiphenylphosphinobutane and 5.3 g of sodium carbonate. The air in the autoclave was replaced with carbon monoxide introduced thereinto in several times, after which carbon monoxide was further introduced to adjust its pressure therein to 30 kg/cm2. The internal temperature was adjusted to 190° C. on a salt bath and the reaction was carried out thereon with stirring for 4 hours. introduced The internal temperature was adjusted to 190° C. on a salt bath

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

Procedure: In an autoclave made of a metal were placed 45.13 g of ortho-chlorobenzotrifluoride, 6.2 g of para-methoxyphenol, 88.5 mg of palladium chloride, 213 mg of 1,4-bisdiphenylphosphinobutane and 5.3 g of sodium carbonate. The air in the autoclave was replaced with carbon monoxide introduced thereinto in several times, after which carbon monoxide was further introduced to adjust its pressure therein to 30 kg/cm2. The internal temperature was adjusted to 190° C. on a salt bath and the reaction was carried out thereon with stirring for 5 hours. introduced The internal temperature was adjusted to 190° C. on a salt bath

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

Procedure: In an autoclave made of a metal were placed 45.13 g of ortho-chlorobenzotrifluoride, 6.2 g of para-methoxyphenol, 88.5 mg of palladium chloride, 213 mg of 1,4-bisdiphenylphosphinobutane and 5.3 g of sodium carbonate. The air in the autoclave was replaced with carbon monoxide introduced thereinto in several times, after which carbon monoxide was further introduced to adjust its pressure therein to 30 kg/cm2. The internal temperature was adjusted to 190° C. on a salt bath and the reaction was carried out thereon with stirring for 5 hours. introduced The internal temperature was adjusted to 190° C. on a salt bath

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

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