HCID 18687706, compound → HCID 18687760, compound

HRID 1872865Notes

Reaction equation

HRID 1872865 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:7](=[O:18])(=[O:17])[C:8]3[C:13]([O:14][C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.Br>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[S:7](=[O:18])(=[O:17])[C:8]3[C:13]([O:14][C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

4

Reactant 1

HCID 18687706HCID 18687706, compound

Product 1

HCID 18687760HCID 18687760, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 260Hydrogen BromideSolvent

Procedure

A stirred solution of 29.4 gm of 3-methoxyphenoxathiin 10,10-dioxide, 5.2 gm of tetrabutylammonium bromide (Aldrich Chemical Co.), and 500 mL of 48% aqueous HBr was refluxed in a 1 liter flask for 6 hours. It was allowed to stir overnight at room temperature and was then refluxed for one additional hour. The contents were cooled to room temperature, and a solid filtered off and washed with waster. There was obtained 26.43 gm of 3-hydroxyphenoxathiin 10,10-dioxide. This was of sufficient purity to be used for further synthetic work. Proton NMR was consistent with the structure. Recrystallization of 0.5 gm from EtOAc/Hexane yielded 0.32 gm, m.p.=213-215°.

Workup

  1. temperaturewas then refluxed for one additional hour
  2. temperatureThe contents were cooled to room temperature
  3. filtrationa solid filtered off
  4. washwashed with waster

Sources & evidence

ORD record
ord-8cacd8892d9d47d68b31cf632643f16c
Source dataset
uspto-grants-2000_08
Patent number
US06110961

Reaction notes

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