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

HRID 396859Notes

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

Conditions

Temperature: 80 °C

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

temperatureThe mixture was cooled down to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography
washeluting with ethyl acetate-hexane (1:4)

Sources & evidence

ORD record: ord-80e4686317214ecb91b2323f86afbb70
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608095B2

Reaction notes

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