Reaktion #159808

Reaktionsgleichung

trifluoroacetic acid

2-isopropylbenzaldehyde

N-bromosuccinamide

→

5-bromo-2-isopropylbenzaldehyde

Ausbeute 58.7%

Lösungsmittel

sulphuric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with dichloromethane (3×30 mL)
2. 2
   Waschenwashed with brine (30 mL)
3. 3
   Trocknendried over sodium sulfate
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe resulting residue was purified by column chromatography

Vorschrift

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).

Quelle