2-(2-fluorophenyl)acetaldehyde

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

Procedure: 2-Fluorophenylacetaldehyde is converted into ethyl 4-(2-fluorophenyl)-4-isopropyl-3-butanoate and hydrolyzed to the acid using the procedure of Example 9. The acid, 4-(2-fluorophenyl)-2-isopropyl-3-butenoic acid, is reacted, via the acid chloride, with m-phenoxybenzyl alcohol to yield m-phenoxybenzyl 4-(2-fluorophenyl)-2-isopropyl-3-butenoate, MS m/e 404.3 (M+). 2-Fluorophenylacetaldehyde is prepared from o-fluoro-β-methoxystyrene via the dimethylacetal using the procedure of Winterfeldt, Berichte 96(12), 3349 (1963).

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

Procedure: 2-Fluorophenylacetaldehyde is converted into ethyl 4-(2-fluorophenyl)-4-isopropyl-3-butanoate and hydrolyzed to the acid using the procedure of Example 9. The acid, 4-(2-fluorophenyl)-2-isopropyl-3-butenoic acid, is reacted, via the acid chloride, with m-phenoxybenzyl alcohol to yield m-phenoxybenzyl 4-(2-fluorophenyl)-2-isopropyl-3-butenoate, MS m/e 404.3 (M+). 2-Fluorophenylacetaldehyde is prepared from o-fluoro-β-methoxystyrene via the dimethylacetal using the procedure of Winterfeldt, Berichte 96(12), 3349 (1963).

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

Procedure: The title compound was prepared from [2-amino-3-(trifluoromethyl)phenyl]-(3-hydroxy-phenyl)methanone and (2-Fluoro-phenyl)-acetaldehyde following the procedure of Example 457: mp 186-187° C.; MS m/z 384, HRMS: calcd for C22H13F4NO+H+, 384.10060; found (ESI, [M+H]+), 384.1.

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

Procedure: A mixture of 2-fluorophenethyl alcohol (Intermediate C1) (commercially available from Aldrich) (2.8 g, 20 mmol) in CH2Cl2 at −10° C. was oxidized by action of pyridinium chlorochromate: PCC (5 g, 23 mmol) in the presence of Celite (10 g) for 1 h at −10° C. and a couple hours at rt. The mixture was filtered through silica gel and the solvent was removed under vacuum to give (2-fluoro-phenyl)-acetaldehyde (Intermediate C2) 2.8 g (99%). at rt The mixture was filtered through silica gel the solvent was removed under vacuum

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

Procedure: A mixture of 2-fluorophenethyl alcohol (Intermediate C1) (commercially available from Aldrich) (2.8 g, 20 mmol) in CH2Cl2 at −10° C. was oxidized by action of pyridinium chlorochromate: PCC (5 g, 23 mmol) in the presence of Celite (10 g) for 1 h at −10° C. and a couple hours at rt. The mixture was filtered through silica gel and the solvent was removed under vacuum to give (2-fluoro-phenyl)-acetaldehyde (Intermediate C2) 2.8 g (99%). at rt The mixture was filtered through silica gel the solvent was removed under vacuum

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

Procedure: 2-(2-Fluorophenyl)ethanol (Ald, 1.0 g) was dissolved in dichloromethane (KANTO, 20 mL) under nitrogen atmosphere and added with Dess-Martin reagent (Alfa Aesar, 3.64 g), followed by stirring at room temperature for 3 hours. Saturated sodium thiosulfate solution was added to the reaction mixture and then extracted with ethyl acetate. The organic layer was washed with saturated sodium hydrogencarbonate solution and brine, and then dried over anhydrous magnesium sulfate. The reaction solution was concentrated under reduced pressure to obtain the target compound as a crude product. extracted with ethyl acetate The organic layer was washed with saturated sodium hydrogencarbonate solution and brine dried over anhydrous magnesium sulfate The reaction solution was concentrated under reduced pressure

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

Procedure: 2-Fluorophenylacetaldehyde is converted into ethyl 4-(2-fluorophenyl)-2-isopropyl-3-butenoate and hydrolyzed to the acid using the procedure of Example 9. The acid, 4-(2-fluorophenyl)-2-isopropyl-3-butenoic acid, is reacted, via the acid chloride, with m-phenoxybenzyl alcohol to yield m-phenoxybenzyl 4-(2-fluorophenyl)-2-isopropyl-3-butenoate, MS m/e 404.3 (M+). 2-Fluorophenylacetaldehyde is prepared from o-fluoro-β-methoxystyrene via the dimethylacetal using the procedure of Winterfeldt, Berichte 96(12), 3349 (1963).