Hydrochloric Acid → N-(4-Acetyl-2-fluorophenyl)methanesulfonamide

HRID 238932

Reaction equation

[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11].[C:14]([O-])(=[O:16])[CH3:15].[Tl+].C(OC=C)CCC.Cl>CN(C=O)C.C1COCC1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[C:6]([C:14](=[O:16])[CH3:15])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of N-(2-Fluoro-4-iodophenyl)methanesulfonamide (13-3, 5 mmol) and palladium(II)acetate (0.15 nM, 0.034 g), 1,3-bisdiphenyl phosphinoprophan (0.3 mM, 0.124 g), thallium(I)acetate (5.5 mM, 1.450 g) and butylvinyl ether (10 mM, 1.3 mL) in DMF (10 mL) was heated at 95° C. for 19 h. The reaction mixture was cooled to room temperature, diluted with THF, treated with 10% HCl (10 mL) and stirred at room temperature. A mixture was diluted with EtOAc, washed with ammonium chloride solution three times and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes as eluant to 3′-Fluoro-4′-(methylsulfonylamino)acetophenone (13-6, LJO-363).

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed with ammonium chloride solution three times
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record: ord-1e154d2223aa4f1f859ba08d87aad887
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642657B2

Linked notes

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