Hydrochloric Acid → 1-[2-Fluoro-4-(4-thiazolyl)phenyl]ethanone

HRID 2086746Notes

Reaction equation

HRID 2086746 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[CH:15][S:16][CH:17]=2)=[CH:9][C:8]=1[F:18])(=O)=O.C(N(CC)CC)C.[CH:28]([O:30]CCCC)=[CH2:29].Cl.C([O-])(O)=O.[Na+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:18][C:8]1[CH:9]=[C:10]([C:13]2[N:14]=[CH:15][S:16][CH:17]=2)[CH:11]=[CH:12][C:7]=1[C:28](=[O:30])[CH3:29]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22316618HCID 22316618, compound

Product 1

HCID 223166161-[2-Fluoro-4-(4-thiazolyl)phenyl]ethanoneYield 87%

Reagents, catalysts & solvents 3

HCID 812191,3-Bis(diphenylphosphino)propaneCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-fluoro-4-(1,3-thiazol-4-yl)phenyl trifluoromethanesulfonate (3.47 g, 10.6 mmol) in DMF (11.7 ml) was added triethylamine (1.29 g, 12.72 mmol), butyl vinyl ether (5.31 g, 53 mmol), 1,3-bis(diphenylphosphino)propane (240 mg, 0.583 mmol), palladium acetate (120 mg, 0.53 mmol) successively, and the mixture was heated at 80° c. for 5 hours. The mixture was cooled down to room temperature. 2N HCl aqueous solution (30 ml) was added, and the mixture was stirred for 1 hour. The mixture was made neutral by addition of NaHCO3, and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:4) to give title compound (2.03 g, 87% yield).

Workup

  1. temperaturethe mixture was heated at 80° c
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting with ethyl acetate-hexane (1:4)

Sources & evidence

ORD record
ord-ab9e966ff8ad4819ad1d3e954bc1d3ee
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

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