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

HRID 2276941Notes

Reaction equation

HRID 2276941 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-f2100a8990e8403e911ae02f22ebfeb8
Source dataset
uspto-grants-2015_09
Patent number
US09133145B2

Reaction notes

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