2-(trifluoromethyl)benzamide

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

Procedure: A solution of 39.2 g of triethyloxonium tetrafluoroborate in 325 ml of methylene chloride is treated with 32.5 g of o-trifluoromethyl-benzamide. After stirring at room temperature for 48 hours the reaction mixture is poured on to a mixture of 10% sodium carbonate solution and ice and the resulting mixture is extracted three times with methylene chloride. The combined extracts are then washed twice with 10% sodium carbonate solution, dried over anhydrous sodium sulphate and evaporated under reduced pressure. The oily, brown residue is distilled in a high vacuum. There is obtained pure ethyl o-trifluoromethyl-benzimidate, b.p. 67° C./0.15 mmHg. the resulting mixture is extracted three times with methylene chloride The combined extracts are then washed twice with 10% sodium carbonate solution dried over anhydrous sodium sulphate evaporated under reduced pressure The oily, brown residue is distilled in a high vacuum

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

Procedure: A solution of 39.2 g of triethyloxonium tetrafluoroborate in 325 ml of methylene chloride is treated with 32.5 g of o-trifluoromethyl-benzamide. After stirring at room temperature for 48 hours the reaction mixture is poured on to a mixture of 10% sodium carbonate solution and ice and the resulting mixture is extracted three times with methylene chloride. The combined extracts are then washed twice with 10% sodium carbonate solution, dried over anhydrous sodium sulphate and evaporated under reduced pressure. The oily, brown residue is distilled in a high vacuum. There is obtained pure ethyl o-trifluoromethyl-benzimidate, b.p. 67° C./0.15 mmHg. the resulting mixture is extracted three times with methylene chloride The combined extracts are then washed twice with 10% sodium carbonate solution dried over anhydrous sodium sulphate evaporated under reduced pressure The oily, brown residue is distilled in a high vacuum

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

Procedure: A solution of 39.2 g of triethyloxonium tetrafluoroborate in 325 ml of methylene chloride is treated with 32.5 g of o-trifluoromethyl-benzamide. After stirring at room temperature for 48 hours the reaction mixture is poured on to a mixture of 10% sodium carbonate solution and ice and the resulting mixture is extracted three times with methylene chloride. The combined extracts are then washed twice with 10% sodium carbonate solution, dried over anhydrous sodium sulphate and evaporated under reduced pressure. The oily, brown residue is distilled in a high vacuum. There is obtained pure ethyl o-trifluoromethyl-benzimidate, b.p. 67° C./0.15 mmHg. the resulting mixture is extracted three times with methylene chloride The combined extracts are then washed twice with 10% sodium carbonate solution dried over anhydrous sodium sulphate evaporated under reduced pressure The oily, brown residue is distilled in a high vacuum

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

Procedure: 1,4-dioxane (20 ml) was added to ethyl 5-bromo-2,3-dihydro-1-benzofuran-7-carboxylate (600 mg), 2-(trifluoromethyl)benzamide (501 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (96 mg), cesium carbonate (1.01 g) and tris(dibenzylideneacetone)dipalladium (114 mg). After degassing, the mixture was stirred at 100° C. under argon atmosphere for 24 hours. The reaction mixture was filtered off on celite, and the solvent was removed under reduced pressure. The resultant residue was purified on silica gel column chromatography to obtain the titled compound (220 mg) as slightly yellow powder. After degassing The reaction mixture was filtered off on celite the solvent was removed under reduced pressure The resultant residue was purified on silica gel column chromatography