Reaction #2314287

Reaction equation

3-(4-hydroxyphenyl)-1-propanol

tetrabromomethane

water

→

1-(4′-hydroxyphenyl)-3-bromopropane

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   workup.ADDITIONis added
2. 2
   Extractionextracted with ethyl acetate
3. 3
   WashThe combined organic layers are washed with brine
4. 4
   Dryingdried over magnesium sulfate
5. 5
   ConcentrationThe solution is concentrated in vacuo

Procedure

To a solution of 3-(4-hydroxyphenyl)-1-propanol 3A (4.0 g) and tripohenylphosphine (7.96 g) in anhydrous dichloromethane (77 mL), cooled to 0° C., is added, dropwise, a solution of tetrabromomethane (9.59 g) in anhydrous dichloromethane (15.4 mL). The reaction mixture gradually warmed to room temperature and allowed to stir overnight. The solution is then poured into water and extracted with ethyl acetate. The combined organic layers are washed with brine and dried over magnesium sulfate. The solution is concentrated in vacuo.

Source