p-Toluenesulfonic acid → 5,6-Dibromo-2,2-dimethylhexahydro-2H-1,3-benzodioxole

HRID 244299Notes

Reaction equation

HRID 244299 reaction equation
[Br:1][CH:2]1[CH:7]([Br:8])[CH2:6][CH:5]([OH:9])[CH:4]([OH:10])[CH2:3]1.CO[C:13](OC)([CH3:15])[CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Br:1][CH:2]1[CH:7]([Br:8])[CH2:6][CH:5]2[O:9][C:13]([CH3:15])([CH3:14])[O:10][CH:4]2[CH2:3]1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 128857644,5-Dibromo-1,2-cyclohexanediol

Product 1

HCID 128857685,6-Dibromo-2,2-dimethylhexahydro-2H-1,3-benzodioxole

Procedure

The compound obtained in Step (10) (20.6 g, 75.62 mmol) was placed in a reaction vessel, and air in the vessel was replaced with nitrogen. 2,2-dimethoxypropane (12.92 ml) and p-toluenesulfonic acid (0.9 g) were added to the vessel, and the mixture was stirred for 3 hours. After the completion of the reaction had been confirmed, the mixture was filtrated through activated alumina, and the filtrate was concentrated under reduced pressure, whereby 5,6-dibromo-2,2-dimethylhexahydro-1,3-benzodioxol was obtained (17.1 g, 72%).

Workup

  1. filtrationthe mixture was filtrated through activated alumina
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-db21b43657454ed49894744823a85fd0
Source dataset
uspto-grants-2014_02
Patent number
US08658459B2

Reaction notes

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