Реакция #52068

Уравнение реакции

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

N-bromosuccinimide

→

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

Выход 97.7%

Растворители

CCl4

water

CH2Cl2

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was heated
2. 2
   Температураat reflux for 1 h
3. 3
   ДругоеThe layers were separated
4. 4
   Промывкаthe aqueous layer was washed with CH2Cl2 (3×)
5. 5
   СушкаThe combined organic solutions were dried (MgSO4)
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated

Методика

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).

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