Iodine → ethyl 6-chloro-8-(methylthio)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 854937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854937
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([S:12](Cl)(=O)=O)[CH:11]=1)[O:8][CH:7]([C:16]([F:19])([F:18])[F:17])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:5]2.II.[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCN(CC)CC.CI>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([S:12][CH3:27])[CH:11]=1)[O:8][CH:7]([C:16]([F:19])([F:18])[F:17])[C:6]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:5]2

Komponenten

7

Edukt 5

HCID 807IodineHCID 6328Methyl iodideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 86599472ethyl 6-chloro-8-(chlorosulfonyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Produkt 1

HCID 69517271ethyl 6-chloro-8-(methylthio)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To benzene (solvent) was added ethyl 6-chloro-8-(chlorosulfonyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate (Step 2, 0.68 g, 1.68 mmol), iodine (0.11 g, 0.84 mmol), and triphenyl phosphine (4.41 g, 16.8 mmol) amd the resulting mixture heated to reflux for 4 h and allowed to cool to RT and stand for 48 h. To this crude reaction was added Et3N (0.58 mL, 0.424 g, 4.20 mmol) and methyl iodide (0.06 mL, 0.13 g, 0.92 mmol). After extractive workup and silica chromatography the title compound was obtained as a yellow, crystalline mass (0.215 g, 36%). 1HNMR (CDCl3-d6/300 MHz) 7.59 (s, 1H), 7.07 (d, J=2.4 Hz, 1H), 6.98 (d, J=2.4 Hz, 1H), 5.78 (q, 1H, J=6.8 Hz), 4.20-4.40 (m, 3H), 2.42 (s, 3H), 1.33 (t, 3H, J=7.3 Hz).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. customTo this crude reaction

Quellen und Nachweise

ORD-Eintrag
ord-854dacd5a15945869312c701ece08c5d
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259266B2

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