1,3-bis(4-fluorophenyl)propane-1,3-dione

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.9 g 1,3-Bis-(4-fluoro-phenyl)-1,3-propandione was dissolved in 45 mL of a solution of 1 N hydrazine in THF and stirred for 2 h at 75° C. The solvent was removed to give 3.6 g of the desired compound. Rt: 1.03 min (method D), (M+H)+: 257 The solvent was removed

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

Procedure: 9.27 g KOtBu was added to 109 mg 18-Krone-6 and 5 mL 4-fluoracetophenone in 150 mL THF. After 30 min at RT 10.7 g 4-fluoro-benzoic acid methyl ester was added and stirred for 3 h at RT. The reaction was decomposed with water and filtered, the filtrate was concentrated and the residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2). The solvent was removed and 3.9 g of the desired compound was obtained. (M+H)+: 261. filtered the filtrate was concentrated the residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2) The solvent was removed

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.9 g 1,3-Bis-(4-fluoro-phenyl)-1,3-propandione was dissolved in 45 mL of a solution of 1 N hydrazine in THF and stirred for 2 h at 75° C. The solvent was removed to give 3.6 g of the desired compound. Rt: 1.03 min (method D), (M+H)+: 257 The solvent was removed

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

Procedure: 9.27 g KOtBu was added to 109 mg 18-Krone-6 and 5 mL 4-fluoracetophenone in 150 mL THF. After 30 min at RT 10.7 g 4-fluoro-benzoic acid methyl ester was added and stirred for 3 h at RT. The reaction was decomposed with water and filtered, the filtrate was concentrated and the residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2). The solvent was removed and 3.9 g of the desired compound was obtained. (M+H)+: 261. filtered the filtrate was concentrated the residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2) The solvent was removed

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

Procedure: 9.27 g KOtBu was added to 109 mg 18-Krone-6 and 5 mL 4-fluoracetophenone in 150 mL THF. After 30 min at RT 10.7 g 4-fluoro-benzoic acid methyl ester was added and stirred for 3 h at RT. The reaction was decomposed with water and filtered, the filtrate was concentrated and the residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2). The solvent was removed and 3.9 g of the desired compound was obtained. (M+H)+: 261. filtered the filtrate was concentrated the residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2) The solvent was removed

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

Procedure: 1,3-Bis-(4-fluoro-phenyl)-propane-1,3-dione and NBS (1.05 eq) were heated neat at 60° C. for 10 minutes then cooled. The resulting mixture was dissolved in ethanol (0.2 M) and treated with thiourea (1.5 eq). It was heated at reflux for 15 hours and cooled to room temperature. It was evaporated to dryness and the residue was partioned between EtOAc and saturated NaHCO3. Organic fraction was dried over MgSO4, filtered and concentrated. The title compound was collected by trituration with heptanes. 1H NMR (400 MHz, DMSO-d6) 6.86-7.01 (m, 4H) 7.22-7.32 (m, 2H) 7.35-7.45 (m, 2H) 8.11 (br. s., 2H). LCMS Method A Rt=1.18 m/z 317.0 (M+1), 315 (M−1). then cooled It was heated at reflux for 15 hours It was evaporated to dryness Organic fraction was dried over MgSO4 filtered concentrated The title compound was collected by trituration with heptanes

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

Procedure: 9.27 g KOtBu was added to 109 mg 18-Krone-6 and 5 mL 4-fluoracetophenone in 150 mL THF. After 30 min at RT 10.7 g 4-fluoro-benzoic acid methyl ester was added and stirred for 3 h at RT. The reaction was decomposed with water and filtered, the filtrate was concentrated and the residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2). The solvent was removed and 3.9 g of the desired compound was obtained. filtered the filtrate was concentrated the residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2) The solvent was removed

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.9 g 1,3-Bis-(4-fluoro-phenyl)-1,3-propandione was dissolved in 45 mL of a solution of 1 N hydrazine in THF and stirred for 2 h at 75° C. The solvent was removed to give 3.6 g of the desired compound. Rt: 1.03 min (method D), (M+H)+: 257 The solvent was removed

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

Procedure: 9.27 g KOtBu was added to 109 mg 18-Krone-6 and 5 mL 4-fluoracetophenone in 150 mL THF. After 30 min at RT 10.7 g 4-fluoro-benzoic acid methyl ester was added and stirred for 3 h at RT. The reaction was decomposed with water and filtered, the filtrate was concentrated and the residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2). The solvent was removed and 3.9 g of the desired compound was obtained. (M+H)+: 261. filtered the filtrate was concentrated the residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2) The solvent was removed