Реакция #43640

Уравнение реакции

7-bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde

copper(I) cyanide

→

desired product

Выход 61.4%

5-formyl-2,3-dihydro-1-benzofuran-7-carbonitrile

Выход 61.4%

Растворители

dimethylacetamide

Условия реакции

Обработка

1. 1
   ТемператураThe reaction was refluxed for 18 hours
2. 2
   Концентрированиеconcentrated under reduced pressure
3. 3
   ПромывкаThe residue was washed well with warm ethyl acetate
4. 4
   КонцентрированиеThe combined ethyl acetate layer were concentrated
5. 5
   Другоеdried
6. 6
   ДругоеThe crude product was purified by flash column chromatography (silica gel, 4:1 and 2:1 hexane:ethyl acetate gradient)

Методика

To a solution of 7-bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde (1.3 g, 4.7 mmol) in dimethylacetamide (2 mL) was added copper(I) cyanide (0.41 g g, 4.7 mmol). The reaction was refluxed for 18 hours, and then concentrated under reduced pressure. The residue was washed well with warm ethyl acetate. The combined ethyl acetate layer were concentrated and dried. The crude product was purified by flash column chromatography (silica gel, 4:1 and 2:1 hexane:ethyl acetate gradient) to afford the desired product (0.5 g, 50%).

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