Triethylamine → 2-Methoxyphenethyl bromide

Participants

Reaction Steps

To a solution of 2-methoxyphenethyl alcohol (5.0 g, 32.6 mmol) in 40 ml of CH2Cl2 was added dimethylaminopyridine (DMAP) (10 mg), Et3N (11.4 ml, 81.8 mmol) and MsCl (5.05 ml, 65.2 mmol) at 0° C. After 1 h, the reaction mixture was poured into hexane and it was washed with aqueous NaHCO3 (2×), water and dried with MgSO4. Upon removal of the solvents, the residue was dissolved in 50 ml of acetone and LiBr (11.34 g, 130.6 mmol) was added. After the solution was heated at reflux for 16 h, it was poured into ether and washed with water, dried with MgSO4, filtered and dried to afford 2-methoxyphenethyl bromide.

Provenance & Evidence