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HCID 118323959, Verbindung → (4-Bromo-2-tert-butoxyquinolin-6-yl)bis(4-chlorophenyl)methanol

HRID 1778217
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1778217
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[O:13])[CH:10]=2)[N:5]=[C:4]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:3]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([Mg]Br)=[CH:29][CH:28]=1>O1CCCC1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([C:30]3[CH:31]=[CH:32][C:27]([Cl:26])=[CH:28][CH:29]=3)([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[OH:13])[CH:10]=2)[N:5]=[C:4]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:3]=1
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Komponenten

4

Edukt 2

HCID 118323959HCID 118323959, VerbindungHCID 178478191HCID 178478191, Verbindung

Produkt 1

HCID 118323945(4-Bromo-2-tert-butoxyquinolin-6-yl)bis(4-chlorophenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of (4-bromo-2-tert-butoxyquinolin-6-yl)(4-chlorophenyl)methanone (4 g, 9.55 mmol, 1.00 equip) in tetrahydrofuran (65 mL). To the resulting mixture was then added (4-chlorophenyl)magnesium bromide (8.2 mL, 1.30 equip, 1 M) dropwise with stirring at 0° C. The resulting solution was stirred for 2 h at 0° C. The reaction was then quenched by the addition of water. The resulting solution was extracted with ethyl acetate (3×150 mL) and the organic layers combined. The resulting mixture was washed with water (2×100 mL) of water and brine (1×100 mL). The resulting mixture was dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column with ethyl acetate:petroleum ether (1:4) to yield (4-bromo-2-tert-butoxyquinolin-6-yl)bis(4-chlorophenyl)methanol as white solid. (ES, m/z): [M+H]+ 532

Aufarbeitung

  1. customInto a 250-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customThe reaction was then quenched by the addition of water
  4. extractionThe resulting solution was extracted with ethyl acetate (3×150 mL)
  5. washThe resulting mixture was washed with water (2×100 mL) of water and brine (1×100 mL)
  6. dry with materialThe resulting mixture was dried over anhydrous sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-6e6081bc41a74b118fa0a6c08f412ca1
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09266835B2

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