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

HRID 1961682Notes

Reaction equation

HRID 1961682 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-a996b42ef23844b39ff244a7ab5cc1a0
Source dataset
uspto-grants-2013_04
Patent number
US08415354B2

Reaction notes

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