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Nitric Acid → 2-(4-Fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-nitrothiophene

HRID 1899088
Notes
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Reaction equation

HRID 1899088 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 103368732-(4-Fluorophenyl)-3-(4-methylsulfonylphenyl)thiophene

Product 1

HCID 106433092-(4-Fluorophenyl)-3-[4-(methylsulfonyl)phenyl]-5-nitrothiophene

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

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

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. concentrationan aqueous solution of sodium bicarbonate, and concentrated
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes