5-Fluoro-2-nitrotoluene → 1-(3,5-Dimethoxyphenylsulphanyl)-3-methyl-4-nitrobenzene

HRID 1603611Notes

Reaction equation

[K].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([SH:12])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1.F[C:14]1[CH:15]=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[C:18]([CH3:20])[CH:19]=1>CN1CCCC1=O>[CH3:11][O:10][C:8]1[CH:7]=[C:6]([S:12][C:14]2[CH:15]=[CH:16][C:17]([N+:21]([O-:23])=[O:22])=[C:18]([CH3:20])[CH:19]=2)[CH:5]=[C:4]([O:3][CH3:2])[CH:9]=1

Participants

Conditions

Temperature: 160 °C

Procedure

0.426 g (0.0021 mol) of 3,5-dimethoxythiophenol potassium salt was dissolved in 7 ml of 1-methyl-2-pyrrolidone, treated with 0.317 g (0.0021 mol) of 5-fluoro-2-nitrotoluene and a spatula tip of Cu powder and stirred at 160° C. for about 5 hrs. Thereafter, the reaction mixture was partitioned in water/diethyl ether and the organic phase was washed with sat. sodium chloride solution and dried over MgSO4. After filtration and removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane 1:9. There was obtained 0.343 g (55%) of 1-(3,5-dimethoxyphenylsulphanyl)-3-methyl-4-nitrobenzene as a yellow oil. MS (EI): me/e=305 (C15H15NO4S+).

Workup

customThereafter, the reaction mixture was partitioned in water/diethyl ether
washthe organic phase was washed with sat. sodium chloride solution
dry with materialdried over MgSO4
filtrationAfter filtration and removal of the solvent the residue
customwas chromatographed on silica gel with ethyl acetate/hexane 1:9

Sources & evidence

ORD record: ord-4b3683f8a4d8499abd1085045ac03c33
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990105

Reaction notes

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