1-bromo-4-tert-butylsulfanylbutane

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

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

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1,4-dibromobutane (commercially available, for example, from Aldrich) (4.7 ml, 40 mmol) in DMF (10 ml) was treated with sodium 2-methyl-2-propanethiolate (commercially available, for example, from Aldrich) (3.36 g, 30 mmol) and the mixture was heated for 23 h at 70° C. The mixture was allowed to cool to room temperature, and partitioned between water and EtOAc. The organic solution was washed with water (×4), aqueous sodium bicarbonate solution, brine, dried (MgSO4), and evaporated. The residue was purified by flash column chromatography on silica (200 g) eluting with 0-50% EtOAc-cyclohexane to give the title compound (1.4 g, 21%): 1H NMR δ (CDCl3) 3.46 (2H, t, J=7 Hz), 2.96 (2H, t, J=7 Hz), 2.15-2.03 (4H, m), 1.44 (9H, s). to cool to room temperature partitioned between water and EtOAc The organic solution was washed with water (×4), aqueous sodium bicarbonate solution, brine dried (MgSO4) evaporated The residue was purified by flash column chromatography on silica (200 g) eluting with 0-50% EtOAc-cyclohexane