1-(bromomethyl)-4-octylbenzene

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

Procedure: PBr3 (0.23 ml) was added drop wise to a stirred solution of the product of Step A (0.082 g; 0.37 mmol) in Et2O (2 ml) at −15° C. The mixture was allowed to warm up to room temperature and the stirring was continued for 4 h. This was poured onto ice (5 g) and the product was extracted with fresh Et2O (2×10 ml). The combined extracts were washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.04 g; 40%) as a colourless solid. 1H-NMR (CDCl3) 7.28 (d, 2H, J=8 Hz); 7.13 (d, 2H, J=8 Hz); 4.48 (s, 2H); 2.57 (t, 2H, J=7.9 Hz); 1.57 (m, 2H); 1.26 (m, 10H); 0.86 (t, 3H, J=7 Hz). This was poured onto ice (5 g) the product was extracted with fresh Et2O (2×10 ml) The combined extracts were washed with 5% NaHCO3, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2, hexane)

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

Procedure: PBr3 (0.23 ml) was added drop wise to a stirred solution of the product of Step A (0.082 g; 0.37 mmol) in Et2O (2 ml) at −15° C. The mixture was allowed to warm up to room temperature and the stirring was continued for 4 h. This was poured onto ice (5 g) and the product was extracted with fresh Et2O (2×10 ml). The combined extracts were washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.04 g; 40%) as a colourless solid. 1H-NMR (CDCl3) 7.28 (d, 2H, J=8 Hz); 7.13 (d, 2H, J=8 Hz); 4.48 (s, 2H); 2.57 (t, 2H, J=7.9 Hz); 1.57 (m, 2H); 1.26 (m, 10H); 0.86 (t, 3H, J=7 Hz). This was poured onto ice (5 g) the product was extracted with fresh Et2O (2×10 ml) The combined extracts were washed with 5% NaHCO3, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2, hexane)

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

Procedure: PBr3 (0.23 ml) was added drop wise to a stirred solution of the product of Step B (0.082 g; 0.37 mmol) in Et2O (2 ml) at −15° C. The mixture was allowed to warm up to room temperature and the stirring was continued for 4 h. This was poured onto ice (5 g) and the product was extracted with fresh Et2O (2×10 ml). The combined extracts were washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.04 g; 40%) as a colourless solid. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=7 Hz); 1.26 (m, 10H); 1.57 (m, 2H); 2.57 (tr, 2H, J=7.9 Hz); 4.48 (s, 2H); 7.13 (d, 2H, J=8 Hz); 7.28 (d, 2H, J=8 Hz). This was poured onto ice (5 g) the product was extracted with fresh Et2O (2×10 ml) The combined extracts were washed with 5% NaHCO3, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2, hexane)

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

Procedure: PBr3 (0.23 ml) was added drop wise to a stirred solution of the product of Step A (0.082 g; 0.37 mmol) in Et2O (2 ml) at −15° C. The mixture was allowed to warm up to room temperature and the stirring was continued for 4 h. This was poured onto ice (5 g) and the product was extracted with fresh Et2O (2×10 ml). The combined extracts were washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.04 g; 40%) as a colourless solid. 1H-NMR (CDCl3) 7.28 (d, 2H, J=8 Hz); 7.13 (d, 2H, J=8 Hz); 4.48 (s, 2H); 2.57 (t, 2H, J=7.9 Hz); 1.57 (m, 2H); 1.26 (m, 10H); 0.86 (t, 3H, J=7 Hz). This was poured onto ice (5 g) the product was extracted with fresh Et2O (2×10 ml) The combined extracts were washed with 5% NaHCO3, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2, hexane)

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

Procedure: PBr3 (0.23 ml) was added drop wise to a stirred solution of the product of Step A (0.082 g; 0.37 mmol) in Et2O (2 ml) at −15° C. The mixture was allowed to warm up to room temperature and the stirring was continued for 4 h. This was poured onto ice (5 g) and the product was extracted with fresh Et2O (2×10 ml). The combined extracts were washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.04 g; 40%) as a colourless solid. 1H-NMR (CDCl3) 7.28 (d, 2H, J=8 Hz); 7.13 (d, 2H, J=8 Hz); 4.48 (s, 2H); 2.57 (t, 2H, J=7.9 Hz); 1.57 (m, 2H); 1.26 (m, 10H); 0.86 (t, 3H, J=7 Hz). This was poured onto ice (5 g) the product was extracted with fresh Et2O (2×10 ml) The combined extracts were washed with 5% NaHCO3, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2, hexane)

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

Procedure: PBr3 (0.23 ml) was added drop wise to a stirred solution of the product of Step B (0.082 g; 0.37 mmol) in Et2O (2 ml) at −15° C. The mixture was allowed to warm up to room temperature and the stirring was continued for 4 h. This was poured onto ice (5 g) and the product was extracted with fresh Et2O (2×10 ml). The combined extracts were washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.04 g; 40%) as a colourless solid. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=7 Hz); 1.26 (m, 10H); 1.57 (m, 2H); 2.57 (tr, 2H, J=7.9 Hz); 4.48 (s, 2H); 7.13 (d, 2H, J=8 Hz); 7.28 (d, 2H, J=8 Hz). This was poured onto ice (5 g) the product was extracted with fresh Et2O (2×10 ml) The combined extracts were washed with 5% NaHCO3, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2, hexane)