Reaction #2069981

Reaction equation

ammonium chloride

sodium hydride

3-(4-bromophenyl)-1-propanol

benzyl bromide

→

4-(3-benzyloxypropyl)bromobenzene

Solvents

benzene

Conditions

Workup

1. 1
   Temperatureunder reflux for 7 hours
2. 2
   Extractionthe mixture was extracted with ethyl acetate (100 mL)
3. 3
   WashThe organic layer was washed with water (40 mL) and brine (40 mL)
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   OtherThe solvent was removed under reduced pressure
6. 6
   Otherthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=20/1)

Procedure

A suspension of sodium hydride (60%, 0.97 g), 3-(4-bromophenyl)-1-propanol (1.0 g) and benzyl bromide (0.69 mL) in benzene (24 mL) was stirred under reflux for 7 hours. After cooling to room temperature, a saturated aqueous ammonium chloride solution (50 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (100 mL). The organic layer was washed with water (40 mL) and brine (40 mL) and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=20/1) to give 4-(3-benzyloxypropyl)bromobenzene (1.4 g).

Source