Reaction #157748

Reaction equation

Water

Potassium hydroxide

1-bromo-2-methylpropane

2-(4-bromophenyl)ethylalcohol

→

title compound

Yield 70.0%

1-Bromo-4-[2-(2-methylpropoxy)ethyl]benzene

Yield 70.0%

Solvents

dimethyl sulfoxide

Conditions

Workup

1. 1
   Extractionfollowed by extraction with dichloromethane
2. 2
   FiltrationThe organic layer was filtered through diatomaceous earth
3. 3
   Otherthe filtrate was evaporated under reduced pressure
4. 4
   OtherThe residue was purified by silica gel column chromatography (hexane only)

Procedure

Potassium hydroxide (1.32 g) and 1-bromo-2-methylpropane (1.04 mL) were added to a solution of 2-(4-bromophenyl)ethylalcohol (140 μL) in dimethyl sulfoxide (2 mL), and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, followed by extraction with dichloromethane. The organic layer was filtered through diatomaceous earth and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane only) to give the title compound as a colorless oil (180 mg, 70%).

Source