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

HRID 129849

Reaktionsgleichung

Reaktionsgleichung von HRID 129849
[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-e00b9406d4074e0cac57050d5114371d
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470870

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