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

HRID 1361434Notes

Reaction equation

HRID 1361434 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-hydroxymethy-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-7a28a5b7fed24fd1b7869c5f77da1917
Source dataset
uspto-grants-2011_02
Patent number
US07880001B2

Reaction notes

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