3-(4-chlorophenyl)propan-1-ol

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

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

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

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

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

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

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: 3-(4-Chlorophenyl)-1-propanol (1.00 g) was dissolved in methylene chloride (30 ml), triphenylphosphine (1.66 g) and N-bromosuccinimide (1.11 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 6 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (50 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone) to give the object product (1.30 g) as a colorless oil. cooling cooling for 6 hr The reaction mixture was washed with water and saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure Diethyl ether (50 ml) was added the precipitated triphenylphosphine oxide was filtered off The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone)

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

Procedure: To a stirred solution of oxalyl chloride (2.04 ml) in dichloromethane (40 ml) at −78° C. was added dimethyl sulphoxide (3.33 ml), and the reaction stirred for 10 min. 3-(4-Chlorophenyl)propanol (2.0 g) in dichloromethane (20 ml) was added and the reaction stirred at −78° C. for 75 min. Triethylamine (11.53 ml) was added, the reaction allowed to warm to room temperature, and stirred for 30 min. Water (150 ml) was added, and the reaction extracted with dichloromethane (2×100 ml). The combined organic extracts were washed with water (3×100 ml), dried over magnesium sulphate (2 g), and the solvent removed in vacuo to yield a yellow oil. This was purified by flash chromatography (silica, eluent dichloromethane) to yield the title compound as a pale yellow oil (0.96 g). the reaction stirred at −78° C. for 75 min stirred for 30 min the reaction extracted with dichloromethane (2×100 ml) The combined organic extracts were washed with water (3×100 ml) dried over magnesium sulphate (2 g) the solvent removed in vacuo to yield a yellow oil This was purified by flash chromatography (silica, eluent dichloromethane)

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

Procedure: To a stirred solution of oxalyl chloride (2.04 ml) in dichloromethane (40 ml) at −78° C. was added dimethyl sulphoxide (3.33 ml), and the reaction stirred for 10 min. 3-(4-Chlorophenyl)propanol (2.0 g) in dichloromethane (20 ml) was added and the reaction stirred at −78° C. for 75 min. Triethylamine (11.53 ml) was added, the reaction allowed to warm to room temperature, and stirred for 30 min. Water (150 ml) was added, and the reaction extracted with dichloromethane (2×100 ml). The combined organic extracts were washed with water (3×100 ml), dried over magnesium sulphate (2 g), and the solvent removed in vacuo to yield a yellow oil. This was purified by flash chromatography (silica, eluent dichloromethane) to yield the title compound as a pale yellow oil (0.96 g). the reaction stirred at −78° C. for 75 min stirred for 30 min the reaction extracted with dichloromethane (2×100 ml) The combined organic extracts were washed with water (3×100 ml) dried over magnesium sulphate (2 g) the solvent removed in vacuo to yield a yellow oil This was purified by flash chromatography (silica, eluent dichloromethane)

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

Procedure: To a stirred solution of 4.15 g (15.8 mmol) of triphenylphosphine in 100 ml of toluene at 0° C., 1.51 ml (15.8 mmol) of bromine was added dropwise. This mixture was stirred for 3 hours then a solution of 3.90 g (22.9 mmol) of Part (a) alcohol and 1.63 ml (15.8 mmol) of pyridine in 20 ml of toluene was added. A solution of 25 ml hexane and 25 ml diethyl ether was added, and a brown mass was formed. The liquid was decanted and concentrated in vacuo. The residue was triturated with hexane:ethyl acetate and triphenylphosphine oxide was precipitated. The solid was filtered and the filtrate was concentrated in vacuo to give a yellow oil. The oil was purified by flash chromatography to obtain 1.80 g (7.72 mmol, 49%) of the desired product. a brown mass was formed The liquid was decanted concentrated in vacuo The residue was triturated with hexane ethyl acetate and triphenylphosphine oxide was precipitated The solid was filtered the filtrate was concentrated in vacuo to give a yellow oil The oil was purified by flash chromatography