Reaction #43530

Reaction equation

boron trichloride

methylene chloride

boron trichloride

3,5-bis(methoxymethyl)styrene

NaOH

→

3,5-bis(chloromethyl)styrene

Yield 54.0%

Solvents

methanol

carbon tetrachloride

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise at 0° C.
2. 2
   Otherto the reaction liquid
3. 3
   Dryingdried with anhydrous magnesium sulfate
4. 4
   OtherResidues obtained by the removal of solvent
5. 5
   Otherwere purified by silica gel column chromatography

Procedure

Subsequently, 2.76 g (14.4 mmol) of 3,5-bis(methoxymethyl)styrene was dissolved in 30 ml of carbon tetrachloride in a reaction vessel of 200 ml, then 40 ml of methylene chloride solution containing 1.0 M boron trichloride was added dropwise at 0° C., and further agitated at 0° C. for 12 hours. After treating the excess boron trichloride by adding methanol to the reaction liquid, the resultant was poured into 150 ml of 5% NaOH solution (added with 100 g of ice). The organic layer was aliquoted and dried with anhydrous magnesium sulfate. Residues obtained by the removal of solvent were purified by silica gel column chromatography to obtain 1.57 g (7.81 mmol) of the target 3,5-bis(chloromethyl)styrene as a transparent liquid. Yield was 54%.

Source