1-Bromo-3-chloropropane → HCID 18965257, compound

Participants

Reaction Conditions

Reaction Steps

Mix 1-bromo-3-chloropropane (5.0 g, 31.76 mmol), absolute ethanol (25 mL), and 3-methyl-l-butanethiol (3.3 g, 31.76 mmol). Place under nitrogen atmosphere and cool to 0° C. In a separate flask, generate sodium ethoxide by carefully adding sodium metal (736 mg, 32 mmol) to absolute ethanol (25 mL) and stirring under nitrogen atmosphere until evolution of nitrogen gas ceases. Add the sodium ethoxide, by dropwise addition, to the above mixture and stir at room temperature for 72 hours. Partition between water and ethyl ether and separate the organic phase. Extract the aqueous phase with ethyl ether (2×50 mL), combine the organic phases and dry (MgSO4). Evaporate in vacuo to yield 3.0 g (52%)3 -chloropropyl isopentyl sulfide as a clear oil; MS (CI/CH4) m/z 181(M+1).

Provenance & Evidence