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

HRID 1094659

Reaktionsgleichung

Reaktionsgleichung von HRID 1094659
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 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8078CyclohexaneLösungsmittel

Versuchsvorschrift

A suspension of 6-bromoquinolin-2-yl-2,2,2-trifluoro-1-methylethyl methanesulfonate (11.97 g, 30 mmol) in cyclohexane (120 ml) was added trimethylaluminum (120 ml, 123 mmol, 1.03M in hexane solution) at room temperature, and the mixture was stirred at room temperature for 1 hour. The reaction was carefully quenched with saturated sodium bicarbonate aqueous solution (30 ml), brine (10 ml) and diluted with ethyl acetate and heptane (200 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 (9.56 g, 80% yield) as colorless oil. 1H NMR (300 MHz, CDCl3) ppm 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 (30 ml), brine (10 ml)
  2. additiondiluted with ethyl acetate and heptane (200 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-44f7ef7c10ab4950ac7a9f7ec3423e9d
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134004B2

Verknüpfte Notizen

Wird geladen…