Triethylamine → 1-(2-Bromoethyl)-2-ethoxybenzene

Temperature

0 °C

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.

1. customat 0° C
2. washIt was washed with 30 ml of water
3. dry with materialdried over MgSO4
4. filtrationfiltered through a plug of silica gel
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in 30 ml of acetone
7. temperatureThe reaction mixture was refluxed for 5 h
8. customvolatiles were removed
9. additionThe residue was added 150 ml of ether
10. washwashed with water (30 ml ×2)
11. dry with materialdried over MgSO4
12. filtrationfiltered through a plug of silica gel
13. concentrationconcentrated

ORD record

ord-f93043d0b6b4407da71f99426c65de65

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06100293