Реакция #937415

Уравнение реакции

sodium thiosulfate

iodine

1-(2-fluoro-4-dimethylbutylsilyloxyphenyl)-2,2-dibromoethylene

n-butyl lithium

→

1-(2-fluoro-4-dimethylbutylsilyloxyphenyl)-2-iodoethyne

Выход 96.2%

Растворители

tetrahydrofuran

tetrahydrofurane

Условия реакции

Обработка

1. 1
   workup.ADDITIONAfter completion of the addition
2. 2
   workup.STIRRINGthe reaction solution was stirred for 3 hours
3. 3
   Другоеwas gradually elevated to room temperature
4. 4
   Экстракцияextracted with heptane
5. 5
   СушкаThe organic layer was dried over anhydrous magnesium sulfate
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   Другоеto afford a brown solid
8. 8
   ДругоеPurification of the solid by a silica gel column chromatography

Методика

To a solution of 26 mmol of 1-(2-fluoro-4-dimethylbutylsilyloxyphenyl)-2,2-dibromoethylene in 50 ml of tetrahydrofurane were added dropwise 134 ml of n-butyl lithium (1.6M), while stirring at -70° C. After completion of the addition, the reaction solution was stirred for 3 hours, 10 ml tetrahydrofuran solution of 30 mmol of iodine were added dropwise and the solution was gradually elevated to room temperature. Afer completion of the agitation, the solution was poured into a sodium thiosulfate solution and extracted with heptane. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a brown solid. Purification of the solid by a silica gel column chromatography gave 25 mmol of 1-(2-fluoro-4-dimethylbutylsilyloxyphenyl)-2-iodoethyne as a yellow solid.

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