Reaction #640547

Reaction equation

1,3-benzodioxole

sulfuryl chloride

→

(1,3-benzodioxol-5-yl)sulfonyl chloride

Yield 16.3%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Otherwhereupon a solid formed
2. 2
   TemperatureThe reaction was cooled
3. 3
   Extractionextracted with methylene chloride
4. 4
   Dryingdried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   Otherto give 7.32 g of crude material as a black oil
8. 8
   OtherThis was chromatographed on silica gel using 20% methylene chloride/hexane

Procedure

To a solution of 4.25 g of anhydrous N,N-dimethylformamide at 0° C. under nitrogen was added 7.84 g of sulfuryl chloride, whereupon a solid formed. After stirring for 15 minutes, 6.45 g of 1,3-benzodioxole was added, and the mixture heated at 100° C. for 2 hours. The reaction was cooled, poured into ice water, extracted with methylene chloride, dried over magnesium sulfate, filtered and concentrated to give 7.32 g of crude material as a black oil. This was chromatographed on silica gel using 20% methylene chloride/hexane to afford 1.9 g of (1,3-benzodioxol-5-yl)sulfonyl chloride.

Source