Acetone → HCID 24866574, compound

HRID 2356691Notes

Reaction equation

HRID 2356691 reaction equation
[Br:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[CH3:12][C:13]([CH3:15])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:13]([CH3:15])([CH3:12])[O:8][C:7](=[O:9])[C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 69725-Bromosalicylic acidHCID 9845Trifluoroacetic anhydride

Product 1

HCID 24866574HCID 24866574, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5 g of 5-bromosalicylic acid were heated under reflux with 6.7 g of acetone in a mixture of 25 ml of trifluoroacetic acid with 5 ml of trifluoroacetic anhydride for 5 h. For workup, the reaction mixture was concentrated under reduced pressure. The residue was neutralized with sodium hydrogencarbonate solution and extracted repeatedly with diethyl ether. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography (silica gel; 9/1 n-heptane/ethyl acetate). 244.1 was obtained.

Workup

  1. concentrationFor workup, the reaction mixture was concentrated under reduced pressure
  2. extractionextracted repeatedly with diethyl ether
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography (silica gel; 9/1 n-heptane/ethyl acetate)
  7. custom244.1 was obtained

Sources & evidence

ORD record
ord-445085e35d7a4591bfbe40ce213377c4
Source dataset
uspto-grants-2010_07
Patent number
US07759366B2

Reaction notes

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