Bromide ion → HCID 18782759, compound

Participants

Reaction Steps

To magnesium turnings (1.82 g, 0.075 mol), covered by dry diethylether (100 mL) under a N2 atmosphere was dropwise added 2-bromotoluene (14.22 g, 0.083 mol). After addition of approximately 1/5 of the bromide the reaction was initiated by gently heating the mixture. The remaining 2-bromotoluene was added over a period of 5 min. When addition was completed the resulting mixture was refluxed for 1.5 h. 1-Acetyl-4-piperidone (9.53 g, 0.068 mol) was added dropwise at ambient temperature and diethylether (100 mL) was added. The reaction mixture was stirred at reflux temperature for 30 min and 1 h at room temperature. 4M NH4Cl (aq) (100 mL) was added and the phases were separated. The organic phase was washed with brine (10 mL), dried (MgSO4) and the solvent evaporated in vacuo. The residual oil was purified on a silica gel column (Eluent: CH2Cl2 /methanol (19:1)) to give the title compound 1.31 g (8%). M.p. 145-146° C.

Provenance & Evidence