Reaktion #52068

Reaktionsgleichung

2-methyl-2-p-tolyl-propionic acid ethyl ester

N-bromosuccinimide

→

2-(4-bromomethyl-phenyl)-2-methyl-propionic acid ethyl ester

Ausbeute 97.7%

Lösungsmittel

CCl4

water

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturat reflux for 1 h
3. 3
   SonstigeThe layers were separated
4. 4
   Waschenthe aqueous layer was washed with CH2Cl2 (3×)
5. 5
   TrocknenThe combined organic solutions were dried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated

Vorschrift

To a solution of 2-methyl-2-p-tolyl-propionic acid ethyl ester (263 mg, 1.27 mmol) and N-bromosuccinimide (272 mg, 1.53 mmol) in CCl4 (15 mL) was added 1,1′-azobis(cyclohexanecarbonitrile) (15.5 mg, 0.06 mmol). The reaction was heated at reflux for 1 h and was diluted with water and CH2Cl2. The layers were separated and the aqueous layer was washed with CH2Cl2 (3×). The combined organic solutions were dried (MgSO4), filtered, and concentrated. Medium pressure chromatography (95:5 hexanes:EtOAc) provided 2-(4-bromomethyl-phenyl)-2-methyl-propionic acid ethyl ester (354 mg). 1H NMR (400 MHz, CDCl3) δ 7.31 (m, 4H), 4.47 (s, 2H), 4.10 (q, 2H), 1.54 (s, 6H), 1.17 (t, 3H).

Quelle