2-(5-bromo-2-methylphenyl)ethanamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-(5-bromo-2-methylbenzyl)methylamine (2.89 g; 13.5 mmol) and sodium carbonate (1.50 g; 14.2 mmol) were added to N,N-dimethylformamide (25 ml). While the mixture was stirred at room temperature, 1-bromo-6,6-dimethyl-2-hepten-4-yne (2.71 g; 13.5 mmol) in N,N-dimethylformamide (5 ml) was added dropwise. The mixture was stirred for 21 hours at room temperature, and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ether (150 ml). The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=50:1), to thereby yield 1.10 g of the target compound as orange oily matter (yield: 24.4%). The mixture was stirred for 21 hours at room temperature concentrated under reduced pressure Water was added to the residue the mixture was extracted with ether (150 ml) The organic layer was washed with saturated brine dried over anhydrous sodium sulfate The solvent was evaporated under reduced pressure the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=50:1)