Reaction #48530

Reaction equation

2,4-dichlorophenol

1,2-dibromoethane

sodium hydroxide

→

1-bromo-2-(2,4-dichlorophenoxy)ethane

Yield 62.0%

Solvents

water

water

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   workup.ADDITIONwas added to the mixture over a period of one hour
3. 3
   Temperatureto reflux for 10 hours
4. 4
   Temperaturecooled
5. 5
   workup.DISTILLATIONthe separated organic layer was distilled

Procedure

A mixture of 2,4-dichlorophenol (105 g, 0.64 mol), 1,2-dibromoethane (157 g, 0.84 mol) and water (500 mL) was heated at reflux, during which time a solution of sodium hydroxide (28.0 g, 0.70 mol) in water (125 mL) was added to the mixture over a period of one hour. The solution was allowed to reflux for 10 hours, cooled and the separated organic layer was distilled to give 1-bromo-2-(2,4-dichlorophenoxy)ethane (106 g, yield 62%). 1HNMR (CDCl3) δ 7.37 (d, 1H, J=2.4 Hz), 7.19 (dd, 1H, J1=8.8 J2=2.4 Hz), 6.88 (d, 1H, J=8.8 Hz), 4.31 (t, 3H, J=6.4 Hz), 3.65 (t, 3H, J=6.4 Hz).

Source