1-bromo-4-(3-methoxypropylsulfonyl)benzene

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium carbonate (2.8 g, 20 mmol) was added to a solution of 3-methoxypropan-1-yl methansulphonate (Method 73; 3.25 g, 19.3 mmol) and 4-bromothiophenol (3.48 g, 18.4 mmol) in DMF (30 ml) and the mixture heated at 40° C. for 4 hours. The mixture was allowed to cool to ambient temperature, poured into water (100 ml) and extracted with EtOAc (2×50 ml). The extracts were combined, washed with saturated aqueous sodium hydrogen carbonate solution (50 ml) and brine (2×50 ml), dried (Chemelut column CE1010) and the volatiles removed by evaporation. The residue was dissolved in MeOH (150 ml) and water (30 ml) and oxone (13.4 g, 21.6 mmol) was added in portions. The mixture was stirred at ambient temperature for 18 hours. The MeOH was evaporated, water (50 ml) added and the solution extracted with DCM (3×50 ml). The extracts were combined, washed with brine (50 ml), dried (Chemelut column CE1010), and evaporated. The residue was purified by flash chromatography on silica gel eluting with iso-hexane:EtOAc (100:0 increasing in polarity to 90:10) to give the title compound (3.32 g, 62%) as a colourless oil. NMR 1.95 (m, 2), 3.19 (m, 2H), 3.26 (s, 3H), 3.41 (t, 2H), 7.70 (d, 2H), 7.78 (d, 2H). to cool to ambient temperature extracted with EtOAc (2×50 ml) washed with saturated aqueous sodium hydrogen carbonate solution (50 ml) and brine (2×50 ml) dried (Chemelut column CE1010) the volatiles removed by evaporation The residue was dissolved in MeOH (150 ml) The MeOH was evaporated water (50 ml) added the solution extracted with DCM (3×50 ml) washed with brine (50 ml) dried (Chemelut column CE1010) evaporated The residue was purified by flash chromatography on silica gel eluting with iso-hexane:EtOAc (100:0 increasing in polarity to 90:10)

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium carbonate (2.8 g, 20 mmol) was added to a solution of 3-methoxypropan-1-yl methansulphonate (Method 68; 3.25 g, 19.3 mmol) and 4-bromothiophenol (3.48 g, 18.4 mmol) in DMF (30 ml) and the mixture heated at 40° C. for 4 hours. The mixture was allowed to cool to ambient temperature, poured into water (100 ml) and extracted with EtOAc (2×50 ml). The extracts were combined, washed with saturated aqueous sodium hydrogen carbonate solution (50 ml) and brine (2×50 ml), dried (Chemelut column CE1010) and the volatiles removed by evaporation. The residue was dissolved in MeOH (150 ml) and water (30 ml) and oxone (13.4 g, 21.6 mmol) was added in portions. The mixture was stirred at ambient temperature for 18 hours. The MeOH was evaporated, water (50 ml) added and the solution extracted with DCM (3×50 ml). The extracts were combined, washed with brine (50 ml), dried (Chemelut column CE1010), and evaporated. The residue was purified by flash chromatography on silica gel eluting with iso-hexane: EtOAc (100:0 increasing in polarity to 90:10) to give the title compound (3.32 g, 62%) as a colourless oil. NMR 1.95 (m, 2H), 3.19 (m, 2H), 3.26 (s, 3H), 3.41 (t, 2H), 7.70 (d, 2H), 7.78 (d, 2H). to cool to ambient temperature extracted with EtOAc (2×50 ml) washed with saturated aqueous sodium hydrogen carbonate solution (50 ml) and brine (2×50 ml) dried (Chemelut column CE1010) the volatiles removed by evaporation The residue was dissolved in MeOH (150 ml) The MeOH was evaporated water (50 ml) added the solution extracted with DCM (3×50 ml) washed with brine (50 ml) dried (Chemelut column CE1010) evaporated The residue was purified by flash chromatography on silica gel eluting with iso-hexane: EtOAc (100:0 increasing in polarity to 90:10)

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium carbonate (2.8 g, 20 mmol) was added to a solution of 3-methoxypropan-1-yl methansulphonate (Method 68; 3.25 g, 19.3 mmol) and 4-bromothiophenol (3.48 g, 18.4 mmol) in DMF (30 ml) and the mixture heated at 40° C. for 4 hours. The mixture was allowed to cool to ambient temperature, poured into water (100 ml) and extracted with EtOAc (2×50 ml). The extracts were combined, washed with saturated aqueous sodium hydrogen carbonate solution (50 ml) and brine (2×50 ml), dried (Chemelut column CE1010) and the volatiles removed by evaporation. The residue was dissolved in MeOH (150 ml) and water (30 ml) and oxone (13.4 g, 21.6 mmol) was added in portions. The mixture was stirred at ambient temperature for 18 hours. The MeOH was evaporated, water (50 ml) added and the solution extracted with DCM (3×50 ml). The extracts were combined, washed with brine (50 ml), dried (Chemelut column CE1010), and evaporated. The residue was purified by flash chromatography on silica gel eluting with iso-hexane: EtOAc (100:0 increasing in polarity to 90:10) to give the title compound (3.32 g, 62%) as a colourless oil. NMR 1.95 (m, 2H), 3.19 (m, 2H), 3.26 (s, 3H), 3.41 (t, 2H), 7.70 (d, 2H), 7.78 (d, 2H). to cool to ambient temperature extracted with EtOAc (2×50 ml) washed with saturated aqueous sodium hydrogen carbonate solution (50 ml) and brine (2×50 ml) dried (Chemelut column CE1010) the volatiles removed by evaporation The residue was dissolved in MeOH (150 ml) The MeOH was evaporated water (50 ml) added the solution extracted with DCM (3×50 ml) washed with brine (50 ml) dried (Chemelut column CE1010) evaporated The residue was purified by flash chromatography on silica gel eluting with iso-hexane: EtOAc (100:0 increasing in polarity to 90:10)

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium carbonate (2.8 g, 20 mmol) was added to a solution of 3-methoxypropan-1-yl methansulphonate (Method 73; 3.25 g, 19.3 mmol) and 4-bromothiophenol (3.48 g, 18.4 mmol) in DMF (30 ml) and the mixture heated at 40° C. for 4 hours. The mixture was allowed to cool to ambient temperature, poured into water (100 ml) and extracted with EtOAc (2×50 ml). The extracts were combined, washed with saturated aqueous sodium hydrogen carbonate solution (50 ml) and brine (2×50 ml), dried (Chemelut column CE1010) and the volatiles removed by evaporation. The residue was dissolved in MeOH (150 ml) and water (30 ml) and oxone (13.4 g, 21.6 mmol) was added in portions. The mixture was stirred at ambient temperature for 18 hours. The MeOH was evaporated, water (50 ml) added and the solution extracted with DCM (3×50 ml). The extracts were combined, washed with brine (50 ml), dried (Chemelut column CE1010), and evaporated. The residue was purified by flash chromatography on silica gel eluting with iso-hexane:EtOAc (100:0 increasing in polarity to 90:10) to give the title compound (3.32 g, 62%) as a colourless oil. NMR 1.95 (m, 2), 3.19 (m, 2H), 3.26 (s, 3H), 3.41 (t, 2H), 7.70 (d, 2H), 7.78 (d, 2H). to cool to ambient temperature extracted with EtOAc (2×50 ml) washed with saturated aqueous sodium hydrogen carbonate solution (50 ml) and brine (2×50 ml) dried (Chemelut column CE1010) the volatiles removed by evaporation The residue was dissolved in MeOH (150 ml) The MeOH was evaporated water (50 ml) added the solution extracted with DCM (3×50 ml) washed with brine (50 ml) dried (Chemelut column CE1010) evaporated The residue was purified by flash chromatography on silica gel eluting with iso-hexane:EtOAc (100:0 increasing in polarity to 90:10)