Dichloromethane → 3,5-Bis(chloromethyl)styrene

HRID 15252Notes

Reaction equation

CO[CH2:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10](COC)[CH:11]=1)[CH:7]=[CH2:8].[CH2:15]([Cl:17])Cl.B(Cl)(Cl)[Cl:19].[OH-].[Na+]>C(Cl)(Cl)(Cl)Cl.CO>[Cl:19][CH2:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH2:15][Cl:17])[CH:11]=1)[CH:7]=[CH2:8]

Participants

Conditions

Temperature: 0 °C

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%.

Workup

additionwas added dropwise at 0° C.
customto the reaction liquid
dry with materialdried with anhydrous magnesium sulfate
customResidues obtained by the removal of solvent
customwere purified by silica gel column chromatography

Sources & evidence

ORD record: ord-303c601ec63140ad9cb114983ef5fc0e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732549B2

Reaction notes

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