Sulfuric Acid → HCID 66823597, compound

HRID 1193231Notes

Reaction equation

HRID 1193231 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([CH:8]2[C:10]3([C:14](=[O:15])[C:13]([CH3:17])([CH3:16])[O:12][C:11]3([CH3:19])[CH3:18])[O:9]2)[CH:7]=1.S(=O)(=O)(O)O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([CH:8]2[C:10](=[O:9])[C:11]([CH3:19])([CH3:18])[O:12][C:13]([CH3:16])([CH3:17])[C:14]2=[O:15])[CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86663666HCID 86663666, compound

Product 1

HCID 66823597HCID 66823597, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(5-bromo-2-fluorophenyl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one (6.60 g, 19.30 mmol) in dichloromethane (8 ml) is added a second ice-cold solution of concentrated sulphuric acid (13.8 ml) dropwise, maintaining temperature below 5° C. The reaction mixture is stirred for a further 30 minutes, then quenched with distilled water (50 ml). After stirring for an additional 10 minutes the organics are removed in vacuo, and the resulting precipitate is filtered then triturated with water. After washing with hexanes the solid is dried to afford 4-(5-bromo-2-fluorophenyl)-2,2,6,6-tetramethylpyran-3,5-dione (4.30 g, 65%).

Workup

  1. temperaturemaintaining temperature below 5° C
  2. customquenched with distilled water (50 ml)
  3. stirringAfter stirring for an additional 10 minutes the
  4. customorganics are removed in vacuo
  5. filtrationthe resulting precipitate is filtered
  6. customthen triturated with water
  7. washAfter washing with hexanes the solid
  8. customis dried

Sources & evidence

ORD record
ord-0be27d0883c643f1a0e90d8cb1f005e8
Source dataset
uspto-grants-2014_03
Patent number
US08680299B2

Reaction notes

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