Реакция #155413

Уравнение реакции

Water

Triethylamine

2-chloro-4-mercaptophenol

4-bromomethyl benzaldehyde

→

4-{[(3-chloro-4-hydroxyphenyl)thio]methyl}benzaldehyde

Выход 84.0%

Растворители

dioxane

Условия реакции

Обработка

1. 1
   Другоеwas then partitioned with ethyl acetate and brine (200 mL each)
2. 2
   ЭкстракцияThe aqueous layer was re-extracted with ethyl acetate (100 mL)
3. 3
   СушкаThe combined organic layers were dried over sodium sulphate
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   Другоеaffording a yellow solid
6. 6
   ДругоеThis was purified by trituration with acetonitrile (5 mL/g) for 30 minutes
7. 7
   ФильтрацияAfter filtration
8. 8
   Другоеthis afforded a light yellow solid as the pure product, 84% yield, 5.27 g

Методика

Triethylamine (5.0 mL, 35.9 mmol) was added dropwise to a solution of 2-chloro-4-mercaptophenol (3.60 g, 22.4 mmol) and 4-bromomethyl benzaldehyde (3.93 g, 19.7 mmol) in dioxane (150 mL) at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 20 hours. Water (100 mL) was added to the reaction mixture and it was then partitioned with ethyl acetate and brine (200 mL each). The aqueous layer was re-extracted with ethyl acetate (100 mL). The combined organic layers were dried over sodium sulphate and concentrated in vacuo affording a yellow solid. This was purified by trituration with acetonitrile (5 mL/g) for 30 minutes. After filtration this afforded a light yellow solid as the pure product, 84% yield, 5.27 g.

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