Trifluoroacetic acid → 5-Bromo-2-isopropylbenzaldehyde

HRID 72626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 72626
FC(F)(F)C(O)=O.[CH:8]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=[O:14])([CH3:10])[CH3:9].[Br:19]NC(=O)CCC(N)=O>S(=O)(=O)(O)O>[Br:19][C:16]1[CH:17]=[CH:18][C:11]([CH:8]([CH3:10])[CH3:9])=[C:12]([CH:15]=1)[CH:13]=[O:14]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 5905362-(Propan-2-yl)benzaldehydeHCID 9834204N-Bromosuccinamide

Produkt 1

HCID 583408355-Bromo-2-isopropylbenzaldehydeAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

To a solution of trifluoroacetic acid (50 ml) and 2-isopropylbenzaldehyde (2.0 g, 13.5 mmol) was added conc. sulphuric acid (98%) (10 ml) at room temperature, followed by N-bromosuccinamide (NBS, 3.6 g 20.2 mmol) in portions. After 2 hrs, the mixture was poured into ice water and extracted with dichloromethane (3×30 mL). The organic layers were combined and neutralized with saturated aqueous sodium bicarbonate, washed with brine (30 mL), dried over sodium sulfate and concentrated. The resulting residue was purified by column chromatography to furnish 5-bromo-2-isopropylbenzaldehyde (1.80 g).

Aufarbeitung

  1. extractionextracted with dichloromethane (3×30 mL)
  2. washwashed with brine (30 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ee557a7feafe40a1af75b03740360b77
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828951B2

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