2,3,4,5,6-pentafluorobenzaldehyde

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

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

Procedure: Compound C is subjected to a second Lindsey-type tri(pentafluorophenyl)porphyrin-ring construction with pentafluorobenzaldehyde and pyrrole, to give the Gable porphyrin, orthodi [mesotri(pentafluorophenyl)porphin]-benzene. In this step, Compound C is reacted again with pyrrole and pentafluorobenzaldehyde in a 1,4,3 molar ratio with BF3 0Et2 catalyst to give the desired ##STR5##

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

Procedure: Production of 2-sulpho tetrafluorobenzoic acid ##STR61## and 2-fluorosulphonyl tetrafluorobenzoyl fluoride ##STR62## 38 g of triethylamine were added dropwise to a well stirred suspension of 50 g of rhodanine and 70 g of pentafluorobenzaldehyde in 100 ml of chloroform, the temperature being held below 40° C. by external cooling. After one hour, the solution was washed with dilute HCl, then water. The solvent was removed and the resultant yellow residue recrystallised from IMS/water to give 82 g of 2,3,4,5,6-pentafluorobenzylidene rhodanine having a melting point of 132-135° C. being held below 40° C. by external cooling the solution was washed with dilute HCl The solvent was removed the resultant yellow residue recrystallised from IMS/water

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared as described in General Method 1 using 2.5 mL of methyl acetoacetate, 1.0 g of NaH 60% dispersion in oil, 12.5 mL of 2.0M n-butyl lithium in hexane, 3.4 mL of pentafluorobenzaldehyde and 75 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 10 minutes at 0° C. then allowed to warm to room temperature overnight. The crude product was triturated from diethyl ether to afford a solid (m.p. 176°-178° C.). 1H NMR (CDCl3) δ 2.89 (dd, 1 H), 3.15 (dd, 1 H), 3.70 (dd, 2 H), 6.02 (dd, 1 H). to warm to room temperature overnight The crude product was triturated from diethyl ether

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

Procedure: The 2,3,4,5,6-pentafluorobenzaldehyde (49.4 g, 252 mmol) was converted to product in a manner substantially analogous to Preparation 59 to yield 52.3 g. (86.0). EA, MS(FD). to yield 52.3 g

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

Procedure: The 2,3,4,5,6-pentafluorobenzaldehyde (49.4 g, 252 mmol) was converted to product in a manner substantially analogous to Preparation 59 to yield 52.3 g. (86.0). EA, MS(FD). to yield 52.3 g

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

Procedure: 9 g of pentafluorobenzaldehyde are condensed on 7 g of diethyl malonate in accordance with the process described in Organic Synthesis vol. III, page 377. 10 g (69%) of diethyl pentafluorobenzylmalonate are obtained which is hydrogenated at ordinary pressure in the presence of palladium on charcoal into diethyl pentafluorobenzylmalonate (92%).

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

Procedure: 9 g of pentafluorobenzaldehyde are condensed on 7 g of diethyl malonate in accordance with the process described in Organic Synthesis vol. III, page 377. 10 g (69%) of diethyl pentafluorobenzylmalonate are obtained which is hydrogenated at ordinary pressure in the presence of palladium on charcoal into diethyl pentafluorobenzylmalonate (92%).

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

Procedure: In the same manner as in Example 7, 433.0 mg of the title compound was obtained as colorless oil from 591.2 mg of Referential Compound 3 and 250 μL of pentafluorobenzaldehyde.

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

Procedure: In the same manner as in Example 7, 433.0 mg of the title compound was obtained as colorless oil from 591.2 mg of Referential Compound 3 and 250 μL of pentafluorobenzaldehyde.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared as described in General Method 1 using 2.5 mL of methyl acetoacetate, 1.0 g of NaH 60% dispersion in oil, 12.5 mL of 2.0M n-butyl lithium in hexane, 3.4 mL of pentafluorobenzaldehyde and 75 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 10 minutes at 0° C. then allowed to warm to room temperature overnight. The crude product was triturated from diethyl ether to afford a solid (m.p. 176°-178° C.). 1H NMR (CDCl3) δ2.89 (dd, 1H), 3.15 (dd, 1H), 3.70 (dd, 2H), 6.02 (dd, 1H). to warm to room temperature overnight The crude product was triturated from diethyl ether

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

Procedure: Compound C is subjected to a second Lindsey-type tri(pentafluorophenyl)porphyrin-ring construction with pentafluorobenzaldehyde and pyrrole, to give the Gable porphyrin, orthodi [mesotri(pentafluorophenyl)porphin]-benzene. In this step, Compound C is reacted again with pyrrole and pentafluorobenzaldehyde in a 1,4,3 molar ratio with BF3 0Et2 catalyst to give the desired ##STR5##