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Stannane, hydroxytrimethyl- → 4-Chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-benzoic acid

HRID 448937
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 448937
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][C:13]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:15]=2[C:16]#[N:17])[C:7]([Cl:22])=[CH:6][C:5]=1[O:23][CH3:24].[OH-].C[Sn+](C)C>ClCCCl>[Cl:22][C:7]1[C:8]([C:10]2[CH:11]=[N:12][C:13]([C:18]([F:19])([F:21])[F:20])=[CH:14][C:15]=2[C:16]#[N:17])=[CH:9][C:4]([C:3]([OH:25])=[O:2])=[C:5]([O:23][CH3:24])[CH:6]=1
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Komponenten

4

Edukt 2

HCID 11217597Stannane, hydroxytrimethyl-2×HCID 686025434-Chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-benzoic acid methyl ester

Produkt 1

HCID 686021944-Chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-benzoic acidAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-benzoic acid methyl ester (1.2 g, 3.2 mmol) and trimethyltin hydroxide (1.75 g, 9.7 mmol) in 1,2-dichloroethane (50 mL) was heated to 80° C. in a sealed tube for 4 hrs. Additional 5.0 eq. of trimethyltin hydroxide was added and the mixture was heated for total of 48 hrs. The mixture was then cooled to rt, quenched with HCl (2N, 40 mL) and diluted with 1,2-dichloroethane. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The residue was purified via silica gel flash column chromatography eluting with dichloromethane:methanol (9:1) to afford 4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-methoxy-benzoic acid (723 mg). NMR (CDCl3), 5, 8.82 (1H, s), 7.94 (1H, s), 7.81 (1H, s), 7.20 (1H, s), 3.90 (3H, s).

Aufarbeitung

  1. temperaturethe mixture was heated for total of 48 hrs
  2. temperatureThe mixture was then cooled to rt
  3. customquenched with HCl (2N, 40 mL)
  4. additiondiluted with 1,2-dichloroethane
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified via silica gel flash column chromatography
  10. washeluting with dichloromethane:methanol (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-1dd40625bd58479cbaec40b240d8078e
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08481738B2

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