fluoro(iodo)methane

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: N-(1S,2S)-[2-(3-Cyanophenyl)-3-(4-fluoromethoxyphenyl)-1-methylpropyl]-2-(4-trifluoromethyl-2-pyridyloxy)-2-methylpropanamide was prepared from N(1S,2S)-[2-(3-cyanophenyl)-3-(4-hydroxyphenyl)-1-methylpropyl]-2-(4-trifluoromethyl-2-pyridyloxy)-2-methylpropanamide (Example 12, Step B) and fluoromethyliodide following the procedure described in Example 4.

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

Procedure: To a solution of 5,6-dichloro-pyridin-3-ol [11860-92-9] (500 mg, 3.05 mmol) and K2CO3 (632 mg, 4.57 mmol) in dry ACN (12 ml) was added fluoro-iodomethane (1.156 ml, 9.15 mmol) at 0° C. The light yellow suspension was stirred for 5 min at 0° C. and then heated up to 120° C. for 30 min. Saturated aq. NH4Cl was added, followed by EtOAc. The organic layer was separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried with Na2SO4, filtered and evaporated to give a brown oil. The crude material was directly used in the next step without further purification. heated up to 120° C. for 30 min The organic layer was separated the aqueous layer was extracted twice with EtOAc The combined organic layers were washed with brine dried with Na2SO4 filtered evaporated to give a brown oil The crude material was directly used in the next step without further purification

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

Procedure: An alternate synthesis of the vinylic fluorinated variant of 3,4-cyclopropyl-heptadecanoic acid can be achieved from the ketone compound described above (FIG. 12). A modified version of the mechanism is from Burton and Greenlimb 1975. J. Org. Chem. 40: 2796-2801; and in Schlosser and Zimmermann 1969. Synthesis 1: 75-76. Fluoromethyltriphenylphosphonium iodide was synthesized in a round-bottomed flask fitted with a water-cooled reflux condenser. The flask was charged with triphenylphosphine and fluoroiodomethane in dry benzene. The resulting solution was refluxed for 64 hr with moderate stirring. Upon completion of the reaction, the white insoluble phosphonium salt was collected on a glass funnel, washed with hot benzene, and dried in a vacuum dessicator for 12 hr. Synthesis 1: 75-76 cooled reflux condenser The resulting solution was refluxed for 64 hr with moderate stirring Upon completion of the reaction the white insoluble phosphonium salt was collected on a glass funnel washed with hot benzene dried in a vacuum dessicator for 12 hr

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