1,4-Dibromobutane → 1-Bromo-4-(tert-butylsulfanyl)butane
Reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.[CH3:7][C:8]([S-:11])([CH3:10])[CH3:9].[Na+]>CN(C=O)C>[CH3:7][C:8]([S:11][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])([CH3:10])[CH3:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
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).