Реакция #710540

Уравнение реакции

HCl

3-chloroaniline

(4-bromo-phenyl)-methanesulfonyl chloride

pyridine

→

C-(4-bromo-phenyl)-N-(3-chloro-phenyl)-methanesulfonamide

Выход 32.3%

Растворители

DCM

Условия реакции

Обработка

1. 1
   Экстракцияextracted with DCM
2. 2
   Фильтрацияfiltered through a separator
3. 3
   Концентрированиеconcentrated
4. 4
   Другоеdry loaded onto silica
5. 5
   Другоеpurified by silica gel column chromatography (0-100% DCM in cyclohexane)

Методика

To a solution of (4-bromo-phenyl)-methanesulfonyl chloride (1.4 g, 5.2 mmol) in DCM (20 mL) at room temperature was added pyridine (1.26 mL, 15.6 mmol) followed by 3-chloroaniline (1.1 mL, 10.4 mmol) and the reaction was stirred at room temperature for 3 hours. 1 M aqueous HCl was added and then extracted with DCM, filtered through a separator, concentrated, dry loaded onto silica and purified by silica gel column chromatography (0-100% DCM in cyclohexane) to give C-(4-bromo-phenyl)-N-(3-chloro-phenyl)-methanesulfonamide (0.61 g, 1.68 mmol). 1H NMR (300 MHz, CDCl3): δ 7.49 (d, 2 H), 7.26 (m, 1 H), 7.13-7.15 (m, 4 H), 6.96-6.98 (m, 1 H), 6.31 (s, 1 H), 4.31 (s, 2 H).

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