Реакция #2348107

Уравнение реакции

Bromine

4-chloro-o-anisidine

→

4-chloro-5-bromo-2-aminoanisole

Выход 33.4%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Другоеquenched with NaOH
2. 2
   ПромывкаThe organic layer was washed with brine
3. 3
   Сушкаdried over MgSO4
4. 4
   Концентрированиеconcentrated
5. 5
   ДругоеPurification by flash chromatography over silica gel (elution with 10% ethyl acetate in hexanes)

Методика

Bromine (26.4 g) was added to a solution of 4-chloro-o-anisidine (23.55 g) in dichloromethane (400 mL) at room temperature. The resulting mixture was stirred for 10 hours and quenched with NaOH. The organic layer was washed with brine, dried over MgSO4, and concentrated. Purification by flash chromatography over silica gel (elution with 10% ethyl acetate in hexanes) gave 11.8 g (33%) of the desired 4-chloro-5-bromo-2-aminoanisole. 1H NMR (300 MHz, CDC13) d 6.94 (s, 1 H), 6.78 (s, 1 H), 3.83 (s, 3 H).

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