1-fluoro-4-iodo-2-methylbenzene

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: Prepared as described for 3,4-bis(benzyloxy)-6-{[5-(trifluoromethyl)pyridin-2-yl]ethynyl}pyridazine (Intermediate 6) from 3,4-bis(benzyloxy)-6-ethynylpyridazine (Intermediate 5) and 1-fluoro-4-iodo-2-methylbenzene in 67% yield. Prepared

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

Procedure: To 8.1 g (51.3 mmol) of potassium permangante in 150 mL of water are added 5.0 g (21.1 mmol) of 2-fluoro-5-iodotoluene. The reaction mixture is heated at reflux for 4 hours. After being cooled to room temperature, the reaction mixture is poured into 250 mL of methylene chloride of sodium bisulfate, and 1N hydrochloric acid. The organic layer is separated, washed with water and dried over sodium sulfate. The solvent is removed in vacuo and the solid triturated with hexane to give 0.86 g (15%) of 2-fluoro-5-iodobenzoic acid as a white solid, m.p. 161°-163° C. The reaction mixture is heated at reflux for 4 hours The organic layer is separated washed with water dried over sodium sulfate The solvent is removed in vacuo the solid triturated with hexane

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

Procedure: The title compound was prepared in substantially the same manner as described in Example 12, step 3 starting from 1-Fluoro-4-iodo-2-methyl-benzene (0.125 g, 0.53 mmol), and 1-Difluoromethoxy-4-ethynyl-benzene (0.09 g, 0.53 mmol), and was obtained as a yellow semi solid, (0.141 g, 96%), and identified by NMR and mass spectral analyses. MS (EI+): 276 (M+). was obtained as a yellow semi solid, (0.141 g, 96%),

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

Procedure: Prepared as described for 3,4-bis(benzyloxy)-6-{[5-(trifluoromethyl)pyridin-2-yl]ethynyl}pyridazine (Intermediate 6) from 3,4-bis(benzyloxy)-6-ethynylpyridazine (Intermediate 5) and 1-fluoro-4-iodo-2-methylbenzene in 67% yield. Prepared

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

Procedure: To 8.1 g (51.3 mmol) of potassium permangante in 150 mL of water are added 5.0 g (21.1 mmol) of 2-fluoro-5-iodotoluene. The reaction mixture is heated at reflux for 4 hours. After being cooled to room temperature, the reaction mixture is poured into 250 mL of methylene chloride of sodium bisulfate, and 1N hydrochloric acid. The organic layer is separated, washed with water and dried over sodium sulfate. The solvent is removed in vacuo and the solid triturated with hexane to give 0.86 g (15%) of 2-fluoro-5-iodobenzoic acid as a white solid, m.p. 161°-163° C. The reaction mixture is heated at reflux for 4 hours The organic layer is separated washed with water dried over sodium sulfate The solvent is removed in vacuo the solid triturated with hexane