Dimethylformamide → 4-(Trifluoromethyl)pyridine-3-carbaldehyde

HRID 717549

Reaktionsgleichung

Reaktionsgleichung von HRID 717549
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14].CN(C)[CH:19]=[O:20]>O1CCCC1>[F:14][C:13]([F:16])([F:15])[C:12]1[C:7]([CH:19]=[O:20])=[CH:8][N:9]=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 199372633-Bromo-4-(trifluoromethyl)pyridineHCID 178418339Butyllithium

Produkt 1

HCID 213547244-(Trifluoromethyl)pyridine-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

n-Butyl lithium (1.65 mL, 0.00265 mol, 1.6 M) was added to a solution of 3-bromo-4-(trifluoromethyl)pyridine (E; 0.5 g, 0.022 mol) in anhydrous tetrahydrofuran (15 mL), at −78° C. The reaction mixture was stirred for 10 min followed by the addition of dimethylformamide (0.2 mL, 0.00265). It was stirred for 30 min at same temperature. The reaction mixture was quenched with a saturated aqueous ammonium chloride solution (25 mL) and the aqueous layer was extracted with ethyl acetate (2×50 mL). The organic extracts were combined and then washed with a saturated aqueous sodium chloride solution (1×50 mL), dried over sodium sulphate and concentrated to afford 4-(trifluoromethyl)nicotinaldehyde. 1H NMR (400 MHz, DMSO-d6) δ 10.39 (s, 1H), 9.25 (s, 1H), 9.10-9.09 (d, J=4 Hz, 1H), 7.95-7.94 (d, J=4 Hz, 1H).

Aufarbeitung

  1. stirringIt was stirred for 30 min at same temperature
  2. customThe reaction mixture was quenched with a saturated aqueous ammonium chloride solution (25 mL)
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  4. washwashed with a saturated aqueous sodium chloride solution (1×50 mL)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fec985d64f5143c6af5eff75947fa8f4
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193724B2

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