Dichloromethane → 2-Chloro-5-iodobenzoyl chloride

HRID 913345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 913345
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4](O)=[O:5].[Cl:12]CCl.C(Cl)(=O)C(Cl)=O>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([Cl:12])=[O:5]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 65578Oxalyl chloride2×HCID 5196382-Chloro-5-iodobenzoic acid

Produkt 1

HCID 47693022-Chloro-5-iodobenzoyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 2 L three-necked round bottom flask with mechanical stirrer, rubber septum with temperature probe and pressure-equalized addition funnel with gas bubbler was charged with 2-chloro-5-iodobenzoic acid (199.41 g, 0.706 mol), dichloromethane (1.2 L, KF=0.003 wt % water) and the suspension was set stirring at ambient temperature. Then N,N-dimethylformamide (0.6 mL, 1.1 mol %) was added followed by oxalyl chloride (63 mL, 0.722 mol, 1.02 equiv) which was added over 11 min. The reaction was allowed to stir at ambient overnight and became a solution. After 18.75 hours, additional oxalyl chloride (6 mL, 0.069 mol, 0.10 equiv) was added to consume unreacted starting material. After 2 hours, the reaction mixture was concentrated in vacuo to afford crude 2-chloro-5-iodobenzoyl chloride as a pale yellow foam which will be carried forward to the next step.

Aufarbeitung

  1. additionwas added over 11 min
  2. stirringto stir at ambient overnight
  3. customto consume unreacted
  4. waitAfter 2 hours
  5. concentrationthe reaction mixture was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fd901d6260e0446eab973e6297b9b0be
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026347B2

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