benzoyl fluoride

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

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

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

Procedure: When the thallous salts of ethyl acetoacetate, 2 -carbethoxycyclopentanone, and 3-methylpentane-2,4-dione, prepared according to Example 1, are treated with acetyl fluoride at room temperature as described in Example 4, ethyl 2-acetylacetoacetate, 2-acetyl-2-carbethoxycyclopentanone, and 3-acetyl-3-methylpentane-2,4-dione, respectively, are obtained in 95% yield. Tribenzoylmethane is prepared by treating the thallous salt of dibenzoylmethane with benzoyl fluoride in the same manner. Acetyldibenzoylmethane is prepared by treating the thallous salt of dibenzoylmethane with acetyl fluoride. respectively, are obtained in 95% yield

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

Procedure: A solution of benzoyl chloride (141 mg, 1 mmol) in CH2Cl2 (5.0 mL) was added to bis(methoxyethyl)aminosulfur trifluoride (567 mg, 3.0 mmol ) under N2 and stirred for 16 h at room temperature. After work-up as above benzoyl fluoride (124 mg, quantitative yield) was obtained. The product was identified by g.c.m.s. M+=124

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

Procedure: A solution of benzoic acid (122 mg, 1 mmol) in CH2Cl2 (5.0 mL) was added to diphenylaminosulfur trifluoride (771 mg, 3.0 mmol ) under N2 and stirred for 16 h at room temperature. After work-up as above benzoyl fluoride (124 mg, quantitative yield) was obtained. The product was identified by g.c.m.s. M+=124

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

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

Procedure: When the thallous salts of ethyl acetoacetate, 2-carbethoxycyclopentanone, and 3-methylpentane-2,4-dione, prepared according to Example 1, are treated with acetyl fluoride at room temperature as described in Example 4, ethyl 2-acetyl-acetoacetate, 2-acetyl-2-carbethoxycyclopentanone, and 3-acetyl-3-methylpentane-2,4-dione, respectively, are obtained in 95% yield. Tribenzoylmethane is prepared by treating the thallous salt of dibenzoylmethane with benzoyl fluoride in the same manner. Acetyldibenzoylmethane is prepared by treating the thallous salt of dibenzoylmethane with acetyl fluoride. respectively, are obtained in 95% yield

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

Procedure: When the thallous salts of ethyl acetoacetate, 2-carbethoxycyclopentanone, and 3-methylpentane-2,4-dione, prepared according to Example 1, are treated with acetyl fluoride at room temperature as described in Example 4, ethyl 2-acetyl-acetoacetate, 2-acetyl-2-carbethoxycyclopentanone, and 3-acetyl-3-methylpentane-2,4-dione, respectively, are obtained in 95% yield. Tribenzoylmethane is prepared by treating the thallous salt of dibenzoylmethane with benzoyl fluoride in the same manner. Acetyldibenzoylmethane is prepared by treating the thallous salt of dibenzoylmethane with acetyl fluoride. respectively, are obtained in 95% yield

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

Procedure: 5.0 g (0.22 mole) of 4'-trifluoromethyl-cyanoacetanilide in 150 ml of dry tetrahydrofuran were stirred at room temperature under nitrogen and treated with 2.0 g (0.066 mole) of sodium hydride 80% oil dispersion. The suspension was stirred for 1 hour at room temperature and then was cooled to -70° C. The flask was equipped with an acetone/dry ice condenser and used as the collecting flask from a distillation apparatus charged with 3.01 ml (0.05 mole) of propiolic acid and 15 g of benzoyl fluoride (0.12 mole), as described in J.A.C.S. (1974), Vol. 96 (18), p. 5855 to 5859. The distillation flask was heated in an oil bath at 50° C. and the liberated propynoyl fluoride passed via an air condenser directly into the cold solution of the carbanion. The mixture was stirred at -70° C. for 1 hour and was then quenched by pouring onto a mixture of dilute hydrochloric acid/ice. The mixture was extracted with ethyl acetate and the extracts were dried over magnesium sulfate. The solvent was removed under reduced pressure and triuration with diethyl ether gave colorless crystals of the title compound. Chromatography of the mother liquors over silica gel, eluting with dichloromethane isolated 2.49 g (40%) of the remainder of the product. was cooled to -70° C The flask was equipped with an acetone/dry ice condenser The distillation flask was heated in an oil bath at 50° C. The mixture was stirred at -70° C. for 1 hour was then quenched by pouring onto a mixture of dilute hydrochloric acid/ice The mixture was extracted with ethyl acetate the extracts were dried over magnesium sulfate The solvent was removed under reduced pressure and triuration with diethyl ether

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

Procedure: 5.0 g (0.22 mole) of 4'-trifluoromethyl-cyanoacetanilide in 150 ml of dry tetrahydrofuran were stirred at room temperature under nitrogen and treated with 2.0 g (0.066 mole) of sodium hydride 80% oil dispersion. The suspension was stirred for 1 hour at room temperature and then was cooled to -70° C. The flask was equipped with an acetone/dry ice condenser and used as the collecting flask from a distillation apparatus charged with 3.01 ml (0.05 mole) of propiolic acid and 15 g of benzoyl fluoride (0.12 mole), as described in J.A.C.S. (1974), Vol. 96 (18), p. 5855 to 5859. The distillation flask was heated in an oil bath at 50° C. and the liberated propynoyl fluoride passed via an air condenser directly into the cold solution of the carbanion. The mixture was stirred at -70° C. for 1 hour and was then quenched by pouring onto a mixture of dilute hydrochloric acid/ice. The mixture was extracted with ethyl acetate and the extracts were dried over magnesium sulfate. The solvent was removed under reduced pressure and triuration with diethyl ether gave colorless crystals of the title compound. Chromatography of the mother liquors over silica gel, eluting with dichloromethane isolated 2.49 g (40%) of the remainder of the product. was cooled to -70° C The flask was equipped with an acetone/dry ice condenser The distillation flask was heated in an oil bath at 50° C. The mixture was stirred at -70° C. for 1 hour was then quenched by pouring onto a mixture of dilute hydrochloric acid/ice The mixture was extracted with ethyl acetate the extracts were dried over magnesium sulfate The solvent was removed under reduced pressure and triuration with diethyl ether

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

Procedure: When the thallous salts of ethyl acetoacetate, 2 -carbethoxycyclopentanone, and 3-methylpentane-2,4-dione, prepared according to Example 1, are treated with acetyl fluoride at room temperature as described in Example 4, ethyl 2-acetylacetoacetate, 2-acetyl-2-carbethoxycyclopentanone, and 3-acetyl-3-methylpentane-2,4-dione, respectively, are obtained in 95% yield. Tribenzoylmethane is prepared by treating the thallous salt of dibenzoylmethane with benzoyl fluoride in the same manner. Acetyldibenzoylmethane is prepared by treating the thallous salt of dibenzoylmethane with acetyl fluoride. respectively, are obtained in 95% yield

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

Procedure: When the thallous salts of ethyl acetoacetate, 2 -carbethoxycyclopentanone, and 3-methylpentane-2,4-dione, prepared according to Example 1, are treated with acetyl fluoride at room temperature as described in Example 4, ethyl 2-acetylacetoacetate, 2-acetyl-2-carbethoxycyclopentanone, and 3-acetyl-3-methylpentane-2,4-dione, respectively, are obtained in 95% yield. Tribenzoylmethane is prepared by treating the thallous salt of dibenzoylmethane with benzoyl fluoride in the same manner. Acetyldibenzoylmethane is prepared by treating the thallous salt of dibenzoylmethane with acetyl fluoride. respectively, are obtained in 95% yield