3-(4-fluorophenyl)sulfanylpropan-1-ol

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

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

Procedure: Part A: A solution of 10 g (78 mmol) of 4-fluorothiophenol and 8 g (86 mM) of 3-chloro-1-propanol in 80 mL of anhydrous DMF was purged with nitrogen for 20 min., then treated with 32 g (234 mM) of potassium carbonate. After one hour, the reaction mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with brine (3×), dried (MgSO4), and concentrated to afford 16 g of crude product. The crude product was chromatographed on silica gel using 30-45% ethyl acetate/hexane to yield 12 g of pure 3-[(4-fluorophenyl)thio]propan-1-ol, m/z=203 (M+NH4). the reaction mixture was concentrated in vacuo the residue was partitioned between ethyl acetate and water The layers were separated the organic layer was washed with brine (3×) dried (MgSO4) concentrated to afford 16 g of crude product The crude product was chromatographed on silica gel using 30-45% ethyl acetate/hexane

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

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

Procedure: 4-Fluorobenzenethiol (788 mg, 6.15 mmol) and 3-bromopropanol (0.535 ml, 6.16 mmol) was dissolved in tetrahydrofuran (20 ml). The solution was added with 1N aqueous solution of sodium hydroxide (6.2 ml, 6.2 mmol) and heated at 80° C. for 3 hours with stirring. The reaction mixture was diluted with a mixed solvent of ethyl acetate-hexane and washed with diluted aqueous solution of sodium hydroxide, water, and then with saturated brine, and dried over magnesium sulfate. Insoluble solids were moved by filtration and the filtrate was concentrated under reduced pressure. The resulting oil was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the title compound as colorless oil (592 mg, yield: 52%). washed with diluted aqueous solution of sodium hydroxide, water with saturated brine, and dried over magnesium sulfate Insoluble solids were moved by filtration the filtrate was concentrated under reduced pressure The resulting oil was purified by silica gel column chromatography (ethyl acetate-hexane)

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

Procedure: Part A: A solution of 10 g (78 mmol) of 4-fluorothiophenol and 8 g (86 mM) of 3-chloro-1-propanol in 80 mL of anhydrous DMF was purged with nitrogen for 20 min., then treated with 32 g (234 mM) of potassium carbonate. After one hour, the reaction mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with brine (3×), dried (MgSO4), and concentrated to afford 16 g of crude product. The crude product was chromatographed on silica gel using 30-45% ethyl acetate/hexane to yield 12 g of pure 3-[(4-fluorophenyl)thio]propan-1-ol, m/z=203 (M+NH4). the reaction mixture was concentrated in vacuo the residue was partitioned between ethyl acetate and water The layers were separated the organic layer was washed with brine (3×) dried (MgSO4) concentrated to afford 16 g of crude product The crude product was chromatographed on silica gel using 30-45% ethyl acetate/hexane