1-(2-bromoethyl)-2-ethoxybenzene

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

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

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1.35 g (8.12 mmol) of 2-ethoxyphenethyl alcohol and 2.05 g (20.03 mmol) of triethylamine in 15 ml of dichloromethane was slowly added 1.86 g (16.24 mmol) of methanesulfonyl chloride at 0° C. The reaction mixture was stirred at 0° C. for 2 h and was poured into 200 ml of mixed solution of hexanelether(1:1). It was washed with 30 ml of water, dried over MgSO4, filtered through a plug of silica gel and concentrated. The residue was dissolved in 30 ml of acetone and 2.82 g (32.48 mmol) of lithium bromide was added slowly at 0° C. The reaction mixture was refluxed for 5 h and volatiles were removed. The residue was added 150 ml of ether, washed with water (30 ml ×2), dried over MgSO4, filtered through a plug of silica gel and concentrated to give 2-ethoxyphenethyl bromide as a colorless oil. at 0° C It was washed with 30 ml of water dried over MgSO4 filtered through a plug of silica gel concentrated The residue was dissolved in 30 ml of acetone The reaction mixture was refluxed for 5 h volatiles were removed The residue was added 150 ml of ether washed with water (30 ml ×2) dried over MgSO4 filtered through a plug of silica gel concentrated