Trifluoroacetic acid → HCID 67071657, compound

HRID 2264012Notes

Reaction equation

HRID 2264012 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]([CH3:15])([CH3:14])[C:11](=[O:13])[CH3:12])[CH:7]=[CH:8][CH:9]=1)[CH3:2].[I:16]N1C(=O)CCC1=O.FC(F)(F)C(O)=O>C(#N)C.C(OCC)(=O)C.CCCCCC>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]([CH3:14])([CH3:15])[C:11](=[O:13])[CH3:12])[CH:7]=[CH:8][C:9]=1[I:16])[CH3:2]

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 120273N-IodosuccinimideHCID 67071649HCID 67071649, compound

Product 1

HCID 67071657HCID 67071657, compoundYield 80.6%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(3-ethoxy-phenyl)-3-methyl-butan-2-one (3.720 g, 18.03 mmol) in acetonitrile (40 mL) was added N-iodosuccinimide (5.679 g, 25.24 mmol) and trifluoroacetic acid (0.7 mL, 9.02 mmol) with stirring under argon. The reaction mixture was stirred at room temperature for 10 min then at 50° C. for 1 h. Upon cooling to room temperature, it was diluted with 10% ethyl acetate in hexane and filtered through a bed of Celite and silica gel. The filtrate was washed with water (1×), saturated solution of sodium bicarbonate (1×), 5% solution of sodium thiosulfate (1×), brine (1×), dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the crude residue by flash chromatography (330 g of silica gel, eluting with 30% ethyl acetate in hexane over 30 min) gave 4.83 g of 3-(3-ethoxy-4-iodo-phenyl)-3-methyl-butan-2-one as off-white solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 10 min
  2. filtrationfiltered through a bed of Celite and silica gel
  3. washThe filtrate was washed with water (1×), saturated solution of sodium bicarbonate (1×), 5% solution of sodium thiosulfate (1×), brine (1×)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude residue
  7. washby flash chromatography (330 g of silica gel, eluting with 30% ethyl acetate in hexane over 30 min)

Sources & evidence

ORD record
ord-4fe8ecb8cef64bdd88fe7d8087eaa3bc
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

Loading…