(2-Ethyl-3-methoxybenzyl)dimethylamine → 3-Dimethylaminomethyl-2-ethylphenol hydrobromide
Reaction equation
[CH2:1]([C:3]1[C:12]([O:13]C)=[CH:11][CH:10]=[CH:9][C:4]=1[CH2:5][N:6]([CH3:8])[CH3:7])[CH3:2].[BrH:15].C(O)(=O)C>>[BrH:15].[CH3:8][N:6]([CH2:5][C:4]1[C:3]([CH2:1][CH3:2])=[C:12]([OH:13])[CH:11]=[CH:10][CH:9]=1)[CH3:7]Participants
3
Procedure
(2-Ethyl-3-methoxybenzyl)dimethylamine (1.30 g, 6.73 mmol) was suspended in 30% hydrogen bromide/acetic acid (10 mL) and heated to reflux with stirring for 21 h. The cooled reaction mixture was triturated and decanted with successive portions of diethyl ether (3×), then triturated with diethyl ether overnight. The solid was collected by filtration, washed with ether and dried to give 3-dimethylaminomethyl-2-ethylphenol hydrobromide (1.37 g, 78%) as a tan solid.
Workup
- temperatureheated
- temperatureto reflux
- custom