Dichloromethane → 4,5-Bis(chloromethyl)-2H-1,3-benzodioxole

HRID 386524Notes

Reaction equation

HRID 386524 reaction equation
O[CH2:2][C:3]1[C:11]2[O:10][CH2:9][O:8][C:7]=2[CH:6]=[CH:5][C:4]=1CO.S(Cl)([Cl:16])=O.[CH2:18]([Cl:20])Cl>>[Cl:16][CH2:2][C:3]1[C:11]2[O:10][CH2:9][O:8][C:7]=2[CH:6]=[CH:5][C:4]=1[CH2:18][Cl:20]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 596054HCID 596054, compound

Product 1

HCID 161004004,5-Bis(chloromethyl)-2H-1,3-benzodioxole

Procedure

A 0° C. solution of (4-hydroxymethyl-1,3-benzodioxol-5-yl)methanol (8.55 g, 47.0 mmoles) from Example 58A in anhydrous methylene chloride (50 mL) was treated dropwise with thionyl chloride (17 mL, 235 mmoles). The mixture was stirred one hour at room temperature and then concentrated under reduced pressure to afford the title compound. MS (DCI) m/z 218 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-74c6da05d8c1496ca81502230a1f3db0
Source dataset
uspto-grants-2013_02
Patent number
US08372841B2

Reaction notes

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