1,6-Dibromohexane → 6-Bromohexylbut-3-enyl ether

Participants

Reaction Steps

A mixture of 1,6-dibromohexane (18.30 g), 3-butene-1-ol (2.15 ml), and tetrabutylammonium bromide (0.81 g) were stirred vigorously with 10N NaOH (25 ml) at room temperature under nitrogen for 18 h. The reaction mixture was partitioned between water and EtOAc. The organic phase was washed with brine, dried (MgSO4), and evaporated to dryness. The residual oil was purified on a silica SPE bond elut cartridge (100 g). The excess 1,6-dibromohexane was eluted with cyclohexane. Elution with 5% diethyl ether in cyclohexane and removal of the solvent under reduced pressure gave the title compound (4.52 g). Tlc-silica (5% diethyl ether in cyclohexane) Rf=0.44.

Provenance & Evidence