HCID 10757175, compound → HCID 18687725, compound

HRID 1872880Notes

Reaction equation

HRID 1872880 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:6](=[O:21])(=[O:20])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][C:10]([O:16]C(C)C)=[CH:9][CH:8]=3>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.Br>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:6](=[O:21])(=[O:20])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][C:10]([OH:16])=[CH:9][CH:8]=3

Participants

4

Reactant 1

HCID 10757175HCID 10757175, compound

Product 1

HCID 18687725HCID 18687725, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 260Hydrogen BromideSolvent

Procedure

A mixture of 3-fluoro-7-isopropoxyphenoxathiin 10,10-dioxide (Example 9) (3.51 g, 11.39 mmoles), tetrabutylammonium hydrogen sulfate (Aldrich) (0.654 g, 1.93 mmoles) and 48% aqueous hydrogen bromide (Acros) (80 mL) was refluxed with stirring for 45 minutes. The reaction was allowed to cool on an ice-bath, and the solid was collected, washed with water and dried in vacuo to give 3.010 g (99%) of 3-fluoro-7-hydroxyphenoxathiin 10,10-dioxide, mp 258-260° C. Recrystallization from ethyl acetate:hexanes gave the analytical sample, m.p. 250-260° C.

Workup

  1. temperaturewas refluxed
  2. temperatureto cool on an ice-bath
  3. customthe solid was collected
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ef965f9c495f4cd8be389c9044e066fc
Source dataset
uspto-grants-2000_08
Patent number
US06110961

Reaction notes

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