3-(4-bromophenoxy)-N,N-dimethylpropan-1-amine

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

Procedure: 4-bromophenol (5.0 g, 28.9 mmol) and 2-dimethylaminoethyl chloride hydrochloride (4.6 g, 31.8 mmol) were combined in a mixture of toluene (100 mL) and 1 M NaOH (50 mL) and heated at reflux for 16 h. The layers were separated and the organic phase was washed with 1 M NaOH, dried (MgSO4) and concentrated to yield 4.2 g of the title compound as a yellow oil which was used without further purification. 1H NMR (400 MHz, CDCl3): δ 2.34 (6H, s), 2.72 (2H, t), 4. 01 (2H, t), 6.73 (2H, m), 7.33 (2H, m). heated at reflux for 16 h The layers were separated the organic phase was washed with 1 M NaOH dried (MgSO4) concentrated