2-(3-fluorophenyl)acetaldehyde

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: 97 mg of 3-fluorobenzeneacetaldehyde and 0.386 mL of isobutyl magnesium bromide (2 M/diethyl ether solution) were dissolved in of 0.2 mL of THF, followed by stirring at room temperature for 1 hour. After completion of the reaction, water was added to the reaction liquid, followed by extraction with chloroform, and the organic layer was then washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using PLC (ethyl acetate:hexane=1:2) to obtain 102 mg (yield 74%) of a title compound as a pale yellow oily substance. was added to the reaction liquid followed by extraction with chloroform the organic layer was then washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue obtained was purified

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

Procedure: 3-Fluorophenylacetaldehyde is converted into ethyl 4-(3-fluorophenyl)-2-isopropyl-3-butenoate using the reaction of Example 9. The ester is hydrolyzed using KOH/MeOH/H2O to 4-(3-fluorophenyl)-2-isopropyl-3-butenoic acid, which is converted to the acid chloride and reacted with α-cyano-m-phenoxybenzyl alcohol to yield α-cyano-m-phenoxybenzyl 4-(3-fluorophenyl)-2-isopropyl-3-butenoate, MS m/e 429 (M+). the reaction of Example 9

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

Procedure: 3-Fluorophenylacetaldehyde is converted into ethyl 4-(3-fluorophenyl)-2-isopropyl-3-butenoate using the reaction of Example 9. The ester is hydrolyzed using KOH/MeOH/H2O to 4-(3-fluorophenyl)-2-isopropyl-3-butenoic acid, which is converted to the acid chloride and reacted with α-cyano-m-phenoxybenzyl alcohol to yield α-cyano-m-phenoxybenzyl 4-(3-fluorophenyl)-2-isopropyl-3-butenoate, MS m/e 429 (M+). the reaction of Example 9

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 (3-Fluoro-phenyl)-acetaldehyde following the procedure of Example 457: MS (ESI) m/z 384; HRMS: calcd for C22H13F4NO+H+, 384.10060; found (ESI, [M+H]+), 384.0992;

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

Procedure: To a stirred suspension of pyridinium chlorochromate (75.5 g, 0.35 mol) in dry dichloromethane (300 ml) under a nitrogen atmosphere was added 2-(3-fluorophenyl)ethanol (43 g, 0.31 mol) dropwise. After the addition the mixture was stirred for 1 hour, allowed to stand overnight then poured down a florisil column. The column was washed with ether and the combined filtrate and washings were evaporated to leave the crude 3-fluorophenyl acetaldehyde as an unstable liquid which was not purified further (34 g), NMR δ 9.75 (1H, t), 7.3 (1H, m), 7.05-6.9 (3H, m), 3.7 (2H, d). After the addition the mixture to stand overnight The column was washed with ether the combined filtrate and washings were evaporated

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

Procedure: 3-Fluorophenylacetaldehyde is converted into ethyl 4-(3-fluorophenyl)-2-isopropyl-3-butenoate using the reaction of Example 9. The ester is hydrolyzed using KOH/MeOH/H2O to 4-(3-fluorophenyl)-2-isopropyl-3-butenoic acid, which is converted to the acid chloride and reacted with α-cyano-m-phenoxybenzyl alcohol to yield α-cyano-m-phenoxybenzyl 4-(3-fluorophenyl)-2-isopropyl-3-butenoate, MS m/e 429 (M+). the reaction of Example 9