Reaktion #50547

Reaktionsgleichung

3-Bromophenol

triethylamine

Acetyl chloride

→

3-bromophenyl acetate

Ausbeute 99.4%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution was cooled in an ice bath
2. 2
   SonstigeAfter 1 h the cooling bath was removed
3. 3
   WaschenThe mixture was washed with hydrochloric acid (1N, 250 mL), water (250 mL), 5% NaHCO3 (250 mL), and brine (250 mL)
4. 4
   SonstigeThe organic layer was dried
5. 5
   Sonstigeevaporated

Vorschrift

3-Bromophenol (100 g, 580 mmol) and triethylamine (104 mL, 750 mmol) were dissolved in dichloromethane (500 mL), and the solution was cooled in an ice bath. Acetyl chloride (49.7 g, 630 mmol) was added dropwise. After 1 h the cooling bath was removed and the mixture was stirred overnight (approx 16 h) at room temperature. The mixture was washed with hydrochloric acid (1N, 250 mL), water (250 mL), 5% NaHCO3 (250 mL), and brine (250 mL). The organic layer was dried and evaporated to provide 124 g (99%) of 3-bromophenyl acetate as a light brown liquid; 1H NMR (CDCl3) δ7.36 (d, 1H), 7.32-7.20 (m, 2H), 7.05 (d, 1H), 2.28 (s, 3H).

Quelle