Trifluoroacetic acid → 5-Bromo-2-isopropylbenzaldehyde

HRID 1258869Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258869
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-e448c0a2908449b2ac104c5dbe6f6b22
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466114B2

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