1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-[(1S)-1-azidoethyl]-2-bromobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-(+)-2-bromo-α-methylbenzyl alcohol (402 mg, 2.0 mmol) and diphenylphosphoryl azide (0.692 ml, 3.2 mmol) in THF (10 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.466 ml, 3.2 mmol). The mixture was heated at 50° C. for overnight, partitioned with H2O and AcOEt, and then adjusted to pH 7 by adding 1M HCl. The organic layer was dried with MgSO4, filtered and evaporated. The residue was purified by silica gel column chromatography [eluting with n-hexane/AcOEt=95/5] to give the title compound (381 mg, 84%).

Provenance & Evidence