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Sodium Iodide → 3-Iodo-5-(4-trifluoromethylphenyl)indole-2-carboxylic acid ethyl ester

HRID 420971
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 420971
[Na+].[I-:2].ClN1C(=O)CCC1=O.[CH2:11]([O:13][C:14]([C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][C:21]([C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=1)=[CH:20][CH:19]=2)=[O:15])[CH3:12].[O-]S([O-])(=S)=O.[Na+].[Na+]>CC(C)=O>[CH2:11]([O:13][C:14]([C:16]1[NH:17][C:18]2[C:23]([C:24]=1[I:2])=[CH:22][C:21]([C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:27][CH:26]=1)=[CH:20][CH:19]=2)=[O:15])[CH3:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 57419913Ethyl 5-(4-(trifluoromethyl)phenyl)-1H-indole-2-carboxylate

Produkt 1

HCID 574199143-Iodo-5-(4-trifluoromethylphenyl)indole-2-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180
Acetone
Lösungsmittel
3×

Versuchsvorschrift

NaI (2.04 g, 14 mmol) in acetone (10 mL) was added dropwise to a stirred solution of N-chlorosuccinimide (1.83 g, 14 mmol) in acetone (10 mL) protected from light. After 15 min, a solution of 5-(4-trifluoromethylphenyl)indole-2-carboxylic acid ethyl ester (3.80 g, 11 mmol; see step (a) above) in acetone (60 mL) was added dropwise, followed by stirring for 2 h at rt. The mixture was poured into Na2S2O3 (aq, 10%, 250 mL) and extracted with EtOAc (200 mL). The combined extracts were washed with NaHCO3 (aq, sat), water and brine, dried (Na2SO4) and concentrated. The residue was treated with petroleum ether to give the sub-title compound. Yield 4.88 g (93%).

Aufarbeitung

  1. extractionextracted with EtOAc (200 mL)
  2. washThe combined extracts were washed with NaHCO3 (aq, sat), water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. additionThe residue was treated with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-2726ce31a1a94c6d992276d562473f9f
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08097623B2

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