Trimethylaluminum → 6-Bromo-2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline

HRID 1693074

Reaktionsgleichung

Reaktionsgleichung von HRID 1693074
CS(O[C:6]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Br:22])[CH:18]=2)[N:13]=1)([CH3:11])[C:7]([F:10])([F:9])[F:8])(=O)=O.[CH3:23][Al](C)C>C1CCCCC1>[Br:22][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:6]([CH3:23])([CH3:11])[C:7]([F:10])([F:9])[F:8])[CH:21]=[CH:20]2

Komponenten

4

Edukt 2

HCID 16682925TrimethylaluminumHCID 574581676-Bromoquinolin-2-yl-2,2,2-trifluoro-1-methylethyl methanesulfonate

Produkt 1

HCID 574581686-Bromo-2-(2,2,2-trifluoro-1,1-dimethylethyl)quinolineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

To a suspension of 1-(6-bromoquinolin-2-yl)-2,2,2-trifluoro-1-methylethyl methanesulfonate (1.40 g, 3.52 mmol) in cyclohexane (14 ml) was added trimethylaluminum (14 ml, 14 mmol, 1.03M in hexane solution) at room temperature, and the mixture was stirred at room temperature for 16 hours. The reaction was carefully quenched with saturated sodium bicarbonate aqueous solution (10 ml), brine (10 ml) and diluted with ethyl acetate (100 ml). After the mixture was stirred for 30 minutes, formed precipitate was removed by celite and washed with ethyl acetate. The filtrate was concentrated and purified through silica gel column chromatography, eluting with hexane only, to furnish the title compound (951 mg, 85% yield) as colorless oil. 1H NMR (300 MHz, CDCl3) δ 1.72 (6H, s), 7.66 (1H, d, J=8.8 Hz), 7.75-7.80 (1H, m), 7.96-8.00 (2H, m), 8.06 (1H, d, J=8.8 Hz). MS (ESI): m/z 318, 320 (M+H)+.

Aufarbeitung

  1. customThe reaction was carefully quenched with saturated sodium bicarbonate aqueous solution (10 ml), brine (10 ml)
  2. additiondiluted with ethyl acetate (100 ml)
  3. stirringAfter the mixture was stirred for 30 minutes
  4. customformed precipitate
  5. customwas removed by celite
  6. washwashed with ethyl acetate
  7. concentrationThe filtrate was concentrated
  8. custompurified through silica gel column chromatography
  9. washeluting with hexane only

Quellen und Nachweise

ORD-Eintrag
ord-9476238cf1374cd2a1091aaee93deee7
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158650B2

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