Reaction #43938

Reaction equation

4-bromo-3,5-dimethylphenol

3-(methylthio)-1-propanol

tributylphosphine

1,1′-(azodicarbonyl)dipiperidine

→

title compound

Yield 87.0%

2-bromo-1,3-dimethyl-5-[3-(methylthio)propoxy]benzene

Yield 87.0%

Solvents

Hexane

toluene

Conditions

Workup

1. 1
   Filtrationthe insoluble substance was filtered off
2. 2
   Concentrationthe filtrate was concentrated under reduced pressure
3. 3
   OtherThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75)

Procedure

To a solution of 4-bromo-3,5-dimethylphenol (4.02 g, 20.0 mmol), 3-(methylthio)-1-propanol (2.12 g, 20.0 mmol) and tributylphosphine (7.97 mL, 32.0 mmol) in toluene (320 mL) was added 1,1′-(azodicarbonyl)dipiperidine (8.07 g, 32.0 mmol), and the mixture was stirred at room temperature for 18 hr under nitrogen atmosphere. Hexane (160 mL) was added to the reaction mixture, the insoluble substance was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-25:75) to give the title compound (5.03 g, yield 87%) as a pale-yellow oil.

Source