Nitric Acid → 2-(4-fluorophenyl)-3-(4-methylsulfonylphenyl)-5-nitrothiophene

HRID 1899088Notes

Reaction equation

[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][CH:14]=[CH:15][C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+]>C(OC(=O)C)(=O)C>[F:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:13][C:14]([N+:1]([O-:4])=[O:2])=[CH:15][C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Nitric acid (d=1.42; 1.6 ml) was added dropwise to a stirred solution of 2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene (6 g) in acetic anhydride (98 ml) at -5° to 0° C. The mixture was stirred for 1 hour at 0° C., treated with sodium bicarbonate (1 g), and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and an aqueous solution of sodium bicarbonate, and concentrated. The residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (20:1) to give yellow crystals of 2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-nitrothiophene (4.4 g).

Workup

concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in ethyl acetate
washwashed with water
concentrationan aqueous solution of sodium bicarbonate, and concentrated
customThe residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (20:1)

Sources & evidence

ORD record: ord-f9c2c34972a04fb1a269c1653ead5f01
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571810

Reaction notes

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