1-(2,3,4,5,6-pentafluorophenyl)ethanone

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

Procedure: Using 2′,3′,4′,5′,6′-pentafluoroacetophenone and thiourea as the raw materials, the same operation as the Example 395(1) gave the title compound.

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

Procedure: Compound 151 was prepared using the following strategy. 2′,3′,4′,5′,6′-Pentafluoroacetophenone, A6, was treated with sodium azide, followed by bromide, to provide 2-bromo-4′-azido-2′,3′,5′,6′-tetrafluoroacetophenone, A151 (Keana, J. F. W.; Cai, S. X. J. Org. Chem., 1990, 55, 3640).

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

Procedure: Compound 151 was prepared using the following strategy. 2′,3′,4′,5′,6′-Pentafluoroacetophenone, A6, was treated with sodium azide, followed by bromide, to provide 2-bromo-4′-azido-2′,3′,5′,6′-tetrafluoroacetophenone, A151 (Keana, J. F. W.; Cai, S. X. J. Org. Chem., 1990, 55, 3640).

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

Procedure: Compound 151 was prepared using the following strategy. 2′,3′,4′,5′,6′-Pentafluoroacetophenone, A6, was treated with sodium azide, followed by bromide, to provide 2-bromo-4′-azido-2′,3′,5′,6′-tetrafluoroacetophenone, A151 (Keana, J. F. W.; Cai, S. X. J. Org. Chem., 1990, 55, 3640).

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

Procedure: Compound 151 was prepared using the following strategy. 2′,3′,4′,5′,6′-Pentafluoroacetophenone, A6, was treated with sodium azide, followed by bromide, to provide 2-bromo-4′-azido-2′,3′,5′,6′-tetrafluoroacetophenone, A151 (Keana, J. F. W.; Cai, S. X. J. Org. Chem., 1990, 55, 3640).

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

Procedure: Compound 151 was prepared using the following strategy. 2′,3′,4′,5′,6′-Pentafluoroacetophenone, A6, was treated with sodium azide, followed by bromide, to provide 2-bromo-4′-azido-2′,3′,5′,6′-tetrafluoroacetophenone, A151 (Keana, J. F. W.; Cai, S. X. J. Org. Chem., 1990, 55, 3640).

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

Procedure: A solution of sodium ethoxide (21% in EtOH, 0.32 gm, 4.76 mmol) was added to a mixture of 1-(pentafluorophenyl)-1-ethanone (5.91 gm, 47.6 mmol, Aldrich) and 4-fluorobenzaldehyde (10.00 gm, 47.6 mmol) stirring in ethanol (100 ml) under argon. The solution was allowed to stir at room temperature for 18 hours, then EtOH was evaporated to afford a yellowish, oily solid. The solid was redissolved in ether, washed with water and brine, then dried over MgSO4, filtered and concentrated to give a yellow residue. The residue was purified by flash chromatography on Merck silica gel in 5% EtOAc/hexane. Fractions containing the product were combined and concentrated to a yellow solid. The solid was recrystallized from hexane to afford the title compound as large yellow crystals (8.220 gm, 52%). EtOH was evaporated to afford a yellowish, oily solid washed with water and brine dried over MgSO4 filtered concentrated to give a yellow residue The residue was purified by flash chromatography on Merck silica gel in 5% EtOAc/hexane Fractions containing the product concentrated to a yellow solid The solid was recrystallized from hexane

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

Procedure: A solution of sodium ethoxide (21% in EtOH, 0.32 gm, 4.76 mmol) was added to a mixture of 1-(pentafluorophenyl)-1-ethanone (5.91 gm, 47.6 mmol, Aldrich) and 4-fluorobenzaldehyde (10.00 gm, 47.6 mmol) stirring in ethanol (100 ml) under argon. The solution was allowed to stir at room temperature for 18 hours, then EtOH was evaporated to afford a yellowish, oily solid. The solid was redissolved in ether, washed with water and brine, then dried over MgSO4, filtered and concentrated to give a yellow residue. The residue was purified by flash chromatography on Merck silica gel in 5% EtOAc/hexane. Fractions containing the product were combined and concentrated to a yellow solid. The solid was recrystallized from hexane to afford the title compound as large yellow crystals (8.220 gm, 52%). EtOH was evaporated to afford a yellowish, oily solid washed with water and brine dried over MgSO4 filtered concentrated to give a yellow residue The residue was purified by flash chromatography on Merck silica gel in 5% EtOAc/hexane Fractions containing the product concentrated to a yellow solid The solid was recrystallized from hexane

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

Procedure: Compound 151 was prepared using the following strategy. 2′,3′,4′,5′, 6′-Pentafluoroacetophenone, A6, was treated with sodium azide, followed by bromide, to provide 2-bromo-4′-azido-2′,3′,5′,6′-tetrafluoroacetophenone, A151 (Keana, J. F. W.; Cai, S. X. J. Org. Chem., 1990, 55, 3640).

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

Procedure: Compound 151 was prepared using the following strategy. 2′,3′,4′,5′, 6′-Pentafluoroacetophenone, A6, was treated with sodium azide, followed by bromide, to provide 2-bromo-4′-azido-2′,3′,5′,6′-tetrafluoroacetophenone, A151 (Keana, J. F. W.; Cai, S. X. J. Org. Chem., 1990, 55, 3640).

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

Procedure: Compound 151 was prepared using the following strategy. 2′,3′,4′,5′, 6′-Pentafluoroacetophenone, A6, was treated with sodium azide, followed by bromide, to provide 2-bromo-4′-azido-2′,3′,5′,6′-tetrafluoroacetophenone, A151 (Keana, J. F. W.; Cai, S. X. J. Org. Chem., 1990, 55, 3640).

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

Procedure: Compound 151 was prepared using the following strategy. 2′,3′,4′,5′,6′-Pentafluoroacetophenone, A6 was treated with sodium azide, followed by bromide, to provide 2-bromo-4′-azido-2′,3′,5′,6′-tetrafluoroacetophenone, A151 (Keana, J. F. W.; Cai, S. X. J. Org. Chem., 1990, 55, 3640).