반응 #52068

반응 방정식

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

N-bromosuccinimide

→

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

수율 97.7%

용매

CCl4

water

CH2Cl2

반응 조건

후처리

1. 1
   온도The reaction was heated
2. 2
   온도at reflux for 1 h
3. 3
   기타The layers were separated
4. 4
   세척the aqueous layer was washed with CH2Cl2 (3×)
5. 5
   건조The combined organic solutions were dried (MgSO4)
6. 6
   여과filtered
7. 7
   농축concentrated

실험 절차

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).

출처