2-(4-fluorophenyl)acetaldehyde

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

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

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4.2 g of sodium hydroxide in 30 ml of water are added to a solution of 35 g of 2-chlorobenzaldehyde in 300 ml of methanol. The reaction mixture is cooled to 10° C. and 36 g of 4-fluorophenylacetaldehyde are rapidly added, during which the solution warms to 30°-40° C. The reaction solution is stirred at 40° C. for 10 hours and then cooled, and the crystals which separate out are filtered off with suction. warms to 30°-40° C cooled the crystals which separate out are filtered off with suction

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

Procedure: To a solution of 672 mg of o-iodoxybenzoic acid in methyl sulfoxide (5 mL) was added 250 μL of 2-(4-fluorophenyl)ethanol and stirring was continued for 3 h. Water (20 mL) was added and the reaction mixture filtered, the filtrate was extracted with ether (3×20 mL), washed with brine (10 mL), dried over magnesium sulfate, and concentrated to give 2-(4-fluorophenyl) ethanal as an unstable oil. The material was immediately dissolved in acetonitrile (3.5 mL) at 0° C. and 264 μL of bromotrimethylsilane and 142 μL of methyl sulfoxide were added. After stirring for 1 h, water (10 mL) was added and the reaction mixture was extracted with ether (3×20 mL), washed with brine (10 mL), dried over magnesium sulfate, and concentrated to give the title compound (220 mg) as an unstable oil which was used immediately without further purification. the reaction mixture filtered the filtrate was extracted with ether (3×20 mL) washed with brine (10 mL) dried over magnesium sulfate concentrated

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

Procedure: To a stirred suspension of pyridinium chlorochromate (6.9 g, 21.4 mmol) in CH2Cl2 (100 ml) was added a solution of 2-(4-fluorophenyl)ethanol (3.0 g, 21.4 mmol) in CH2Cl2 (10 ml). The resulting suspension was stirred for 2 hours at room temperature and was then diluted with ether. The resulting suspension was filtered through a pad of Celite and washed with ether. The solvents were removed under reduced pressure to yield the crude title compound as a green oil (2.6 g, 86%), which was used as such for further reaction. The resulting suspension was filtered through a pad of Celite washed with ether The solvents were removed under reduced pressure

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

Procedure: To a stirred suspension of pyridinium chlorochromate (6.9 g, 21.4 mmol) in CH2Cl2 (100 ml) was added a solution of 2-(4-fluorophenyl)ethanol (3.0 g, 21.4 mmol) in CH2Cl2 (10 ml). The resulting suspension was stirred for 2 hours at room temperature and was then diluted with ether. The resulting suspension was filtered through a pad of Celite and washed with ether. The solvents were removed under reduced pressure to yield the crude title compound as a green oil (2.6 g, 86%), which was used as such for further reaction. The resulting suspension was filtered through a pad of Celite washed with ether The solvents were removed under reduced pressure

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of p-tolyl hydrazine hydrochloride (3 g, 0.0189 mol), 4-fluorophenyl acetaldehyde (3 g, 0.0227 mol) and ethanol (50 mL) was heated at 80° C. for 1 h. After completion of reaction (monitored by TLC), the mixture was cooled to RT, basified with potassium hydroxide solution, and extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by column chromatography (15% EtOAc:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch) to provide the desired compound as a brown colored oil (2 g, 47% yield). After completion of reaction (monitored by TLC) the mixture was cooled to RT extracted with EtOAc (3×100 mL) The organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure purified by column chromatography (15% EtOAc:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch)

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.5 g of sodium hydroxide in 30 ml of water are added to a solution of 40 g of 3-cyclohexenecarbaldehyde in 300 ml of methanol. The reaction mixture is cooled to 10° C., and 49.7 g of 4-fluorophenylacetaldehyde are rapidly added dropwise, the temperature of the solution not exceeding 30° C. After the mixture has been stirred for 2 hours at room temperature, 200 ml of water are added to the colorless reaction solution and the resulting emulsion is extracted by shaking with methyl tert-butyl ether. The organic phase is separated off, and 34 g (41%) of Z-2-(4-fluorophenyl)-3-(3-cyclohexenyl)-propenal are obtained under 0.5 mbar and at 136°-142° C. by distillation of the remaining residue. exceeding 30° C the resulting emulsion is extracted by shaking with methyl tert-butyl ether The organic phase is separated off

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4.2 g of sodium hydroxide in 30 ml of water are added to a solution of 26.5 g of benzaldehyde in 300 ml of methanol. The reaction mixture is cooled to 10° C., and 36 g of 4-fluorophenylacetaldehyde are rapidly added, during which the solution rises to 30°-40° C. The reaction solution is stirred at 40° C. for 10 hours and then cooled and the crystals which have separated out are filtered off with suction. 31.6 g (56%) of E/Z-2-(4-fluorophenyl)-3-phenylpropenal of melting point 87°-94° C. are obtained. rises to 30°-40° C cooled the crystals which have separated out are filtered off with suction

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: To p-fluorophenethyl alcohol (4.5 g, 31.9 mmol) in 50 ml dichloromethane is added sodium acetate (0.5 g, 6.2 mmol) and pyridinium chlorochromate (10.4 g, 48.1 mmol) with stirring, at RT and under nitrogen. The reaction mixture is stirred for about 2 hours and then filtered through a column of Florisil using dichloromethane. The filtrate is dried, concentrated under vacuum and distilled (short path) to yield p-fluorophenylacetaldehyde (fraction at 90°, 3.5 mm Hq.). The reaction mixture is stirred for about 2 hours filtered through a column of Florisil The filtrate is dried concentrated under vacuum distilled (short path)