Sulfuric Acid → 1-Bromo-5-fluoro-2-iodo-3-nitrobenzene

HRID 375221

Reaktionsgleichung

Reaktionsgleichung von HRID 375221
[F:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:5](N)=[C:4]([Br:12])[CH:3]=1.S(=O)(=O)(O)O.N([O-])=O.[Na+].[I-:22].[K+]>O.C(OCC)(=O)C>[I:22][C:5]1[C:4]([Br:12])=[CH:3][C:2]([F:1])=[CH:8][C:7]=1[N+:9]([O-:11])=[O:10]

Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 2920042-Bromo-4-fluoro-6-nitroanilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 194297701-Bromo-5-fluoro-2-iodo-3-nitrobenzeneAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Mix 4-fluoro-2-bromo-6-nitroaniline (15.5 g, 66.0 mmol) and 50% sulfuric acid (200 mL) and cool to 0°-5° C. Add, by dropwise addition, a solution of sodium nitrite (6.0 g, 86.4 mmol) in water (50 mL). Stir for 30 minutes and add solid potassium iodide (29 g, 173 mmol). Take up the product in ethyl acetate (300 mL), wash with saturated sodium hydrogen carbonate (2×200 mL), saturated sodium metabisulfite (2×200 mL) and water (200 mL). Dry (MgSO4), evaporate the solvent in vacuo and purify by silica gel chromatography to give 1-iodo-2-nitro-4-fluoro-6-bromobenzene as a yellow crystalline solid (17.81 g, 76%); mp 75°-76° C.

Aufarbeitung

  1. temperaturecool to 0°-5° C
  2. additionAdd, by dropwise addition
  3. washwash with saturated sodium hydrogen carbonate (2×200 mL), saturated sodium metabisulfite (2×200 mL) and water (200 mL)
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. custompurify by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3fa3401d2ff347739d876e5ad8456eeb
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05484814

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