Dichloromethane → 4-Bromo-5-nitrothiophene-2-carbaldehyde

HRID 723228

Reaktionsgleichung

Reaktionsgleichung von HRID 723228
[N+:1]([O-:4])([O-])=[O:2].[K+].[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[O:13])[S:10][CH:11]=1.C(Cl)Cl>OS(O)(=O)=O>[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[O:13])[S:10][C:11]=1[N+:1]([O-:4])=[O:2]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 24434Potassium NitrateHCID 877924-Bromothiophene-2-carbaldehyde

Produkt 1

HCID 218862814-Bromo-5-nitrothiophene-2-carbaldehydeAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of potassium nitrate (110 g, 1.09 mol) in H2SO4 (550 mL, conc.) was added to a solution of 4-bromo-thiophene-2-carbaldehyde (207.6 g, 1.08 mol) in H2SO4 (1.1 L, conc.) at CH2Cl2 (5 mL, anhydrous) at 0° C. over a 45 minute period. The reaction mixture was stirred 0° C. for 2 hrs, then stirred overnight at rt. The reaction mixture was poured over ice, filtered, and washed with water and hexanes. The yellow solid was dried overnight to afford the title compound (251.4 g, 98.6%). 1H-NMR (DMSO-d6): δ 9.90 (s, 1H), 8.56 (s, 1H).

Aufarbeitung

  1. stirringstirred overnight at rt
  2. additionThe reaction mixture was poured over ice
  3. filtrationfiltered
  4. washwashed with water and hexanes
  5. customThe yellow solid was dried overnight

Quellen und Nachweise

ORD-Eintrag
ord-d103f6c77f19491694048527fd202014
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138530B2

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