Allyl bromide → HCID 69119699, compound

Participants

Reaction Steps

To a stirred solution of 3-bromophenyl methyl sulfone (Tet. Left. 1994, 35, 9063; 4.74 g) in THF (200 ml) at −78° under nitrogen was added a solution of lithium bis(trimethylsilyl)amide (19 ml, 1.06M in THF) dropwise. The mixture was stirred for 25 min before a solution of allyl bromide (2.44 g) in THF (10 ml) was added. The mixture was allowed to stir at −78° for 1.5 h then quenched with an aqueous solution of ammonium chloride. The product was extracted with EtOAc, and the organic phase washed with brine, dried (MgSO4) and evaporated to dryness. The residual oil was purified on a silica SPE bond elut cartridge (100 g) using a gradient of 5%-40% diethyl ether in cyclohexane (Gradmaster™). The appropriate fractions were evaporated to give the title compound (1.66 g) LCMS RT=3.40 min.

Provenance & Evidence