Реакция #361526

Уравнение реакции

3-chloro-1,4-oxathiane

3,4-dichlorophenylmagnesium bromide

3,4-dichlorobromobenzene

magnesium

ammonium chloride

1,4-oxathiane

→

3-(3,4-dichlorophenyl)-1,4-oxathiane

Растворители

benzene

Условия реакции

Обработка

1. 1
   Другоеthe temperature of reaction below 10° C
2. 2
   Другоеthe organic phase was separated
3. 3
   Промывкаthe aqueous washed with ether (2×40 ml)
4. 4
   СушкаThe combined organic extracts were dried (MgSO4)
5. 5
   Другоеpurified by flash chromatography on silica eluting with toluene/hexane (1:1)

Методика

A stirred solution of 3,4-dichlorophenylmagnesium bromide [prepared from 3,4-dichlorobromobenzene (10.2 g, 45 mmol) and magnesium (1.1 g, 45 mmol) in the usual fashion] was treated with a solution of 3-chloro-1,4-oxathiane [prepared from 1,4-oxathiane (2.6 g, 25 mmol) using the method of Tuleen and Bennet J. Het. Chem. 1969, 6, 115] in benzene (30 ml), maintaining the temperature of reaction below 10° C. The mixture was allowed to stand at room temperature overnight. It was then poured into ammonium chloride solution (50 ml), the organic phase was separated and the aqueous washed with ether (2×40 ml). The combined organic extracts were dried (MgSO4) and purified by flash chromatography on silica eluting with toluene/hexane (1:1) to give 3-(3,4-dichlorophenyl)-1,4-oxathiane (4.5 g), as colourless crystals, m.p. 65°-68° C.;

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