Sulfuric Acid → HCID 86599500, compound

HRID 855125Notes

Reaction equation

HRID 855125 reaction equation
[CH2:1]([O:3][C:4]#[C:5][C:6]1[CH:7]=[C:8]([O:23][C:24]([F:27])([F:26])[F:25])[CH:9]=[C:10]2[C:15]=1[O:14][CH:13]([C:16]([F:19])([F:18])[F:17])[C:12]([C:20]([OH:22])=[O:21])=[CH:11]2)[CH3:2].[OH:28]S(O)(=O)=O>CC(C)=O.O.[Cl-].[Na+].O>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:7]=[C:8]([O:23][C:24]([F:25])([F:27])[F:26])[CH:9]=[C:10]2[C:15]=1[O:14][CH:13]([C:16]([F:17])([F:18])[F:19])[C:12]([C:20]([OH:22])=[O:21])=[CH:11]2)[CH3:2]

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 86599501HCID 86599501, compound

Product 1

HCID 86599500HCID 86599500, compoundYield 198.8%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of the crude product from Step 1 (2.13 g) in a mixture of acetone (80 mL) and H2O (10 mL) was added H2SO4 (0.250 g, 2.55 mmole) and the resulting mixture was stirred at room temperature for 2.5 hrs. Brine (200 mL) was added and the mixture was extracted with EtOAc (2×100 mL). The combined extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give 2.10 g of the crude product as a yellow oil: ESLRMS m/z 414.0 (M+H, C16H12F6O6, Calc'd 415.0).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×100 mL)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86ca086b5c27490dafa0b61994c9b726
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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