تفاعل #2507822

معادلة التفاعل

p-toluenesulfonyl cyanide

n-butyl-lithium

7-bromo-6,6′-difluoro-3′-propyl-3,4,3′,4′-tetrahydro-2H,2′H-[3,7′]bichromenyl

→

6,6′-difluoro-3′-propyl-3,4,3′,4′-tetrahydro-2H,2′H-[3,7]bichromenyl-7-carbonitrile

المذيبات

ether

THF

hexane

THF

ظروف التفاعل

المعالجة

1. 1
   workup.WAITThe batch is left
2. 2
   أخرىdoes not exceed −65° C
3. 3
   workup.WAITAfter 30 min
4. 4
   غسيلwashed with dil. hydrochloric acid
5. 5
   تجفيفphase is dried over sodium sulfate
6. 6
   أخرىevaporated
7. 7
   أخرىthe crude product is chromatographed on silica gel with heptane/toluene (2:3)

الإجراء التجريبي

1.4 g (3.31 mmol) of 7-bromo-6,6′-difluoro-3′-propyl-3,4,3′,4′-tetrahydro-2H,2′H-[3,7′]bichromenyl are dissolved in 20 ml of THF, and 3 ml (4.8 mmol) of a 15 percent solution of n-butyl-lithium in hexane are added at −50° C. The batch is left to stir for 2 h at −70° C., and a solution of 0.9 g (5.00 mmol) of p-toluenesulfonyl cyanide in 10 ml of THF is subsequently added at such a rate that the temperature does not exceed −65° C. After 30 min, the batch is allowed to thaw, diluted with ether and washed with dil. hydrochloric acid. The org. phase is dried over sodium sulfate and evaporated, and the crude product is chromatographed on silica gel with heptane/toluene (2:3), giving 6,6′-difluoro-3′-propyl-3,4,3′,4′-tetrahydro-2H,2′H-[3,7]bichromenyl-7-carbonitrile as colourless crystals of m.p. 122° C.

المصدر