Allyl bromide → 3-(3-Bromo-2,2-bis(bromomethyl)propoxy)prop-1-ene

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (1.67 g, 42 mmol) was added carefully to 3-bromo-2,2-bis(bromomethyl)propanol (9.75 g, 30 mmol) and allyl bromide (12.9 ml, 150 mmol) in dry and degassed DMF (40 ml) under nitrogen at 0° C. The temperature was then increased to room temperature (22° C.) and the reaction mixture was stirred for another 3 h. The reaction mixture was then carefully added to an aqueous saturated NH4Cl (50 ml). The H2O-phase was then extracted with diethyl ether (2×50 ml) and the combined organic phases were washed with H2O (5×50 ml) and then brine (50 ml). The organic phase was dried with Na2SO4 followed by filtration. The volatile materials were removed at reduced pressure to give a pale yellow oil (9.7 g). Column chromatography on silica (heptane:EtOAc 9:1) gave 6.6 g (62%) of the product as a clear oil. 1H-NMR (CDCl3); 5.93 (m, 1H), 5.28 (m, 2H), 4.05 (d, 2H), 3.58 (s, 6H), 3.52 (s, 2H).

Provenance & Evidence