Реакция #46949

Уравнение реакции

5-iodo-2-isopropyl-4-methoxy-phenol

KOtBu

phenoxide

toluene-4-sulfonic acid cyanomethyl ester

→

(5-iodo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile

Выход 82.0%

Растворители

THF

THF

THF

Условия реакции

Обработка

1. 1
   Другоеdid not exceed 6 degrees C
2. 2
   ДругоеThe reaction mixture was partitioned between n-heptane (50 mL) and water (50 mL)
3. 3
   workup.DISTILLATIONthe organic layer was displaced into n-heptane by distillation (to a pot temperature of 97 degrees C
4. 4
   КонцентрированиеThe concentrate in n-heptane
5. 5
   Температураwas cooled slowly to ambient temperature
6. 6
   Промывкаthe resulting crystalline solid was washed with n-heptane
7. 7
   Другоеdried

Методика

To a cold (1 degree C.) solution of 10.0 g of 5-iodo-2-isopropyl-4-methoxy-phenol in 25 mL THF was added 41.3 mL of 1N KOtBu in THF at a rate such that the internal temperature did not exceed 6 degrees C. To the resultant phenoxide solution was added a solution of 7.2 g of toluene-4-sulfonic acid cyanomethyl ester in 25 mL THF, and the reaction mixture was allowed to warm slowly to ambient temperature overnight. The reaction mixture was partitioned between n-heptane (50 mL) and water (50 mL), and the organic layer was displaced into n-heptane by distillation (to a pot temperature of 97 degrees C.). The concentrate in n-heptane was cooled slowly to ambient temperature and the resulting crystalline solid was washed with n-heptane and dried. In this manner, 9.26 g of (5-iodo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile was isolated (81%): m.p. 67.5-68.8 degrees C.; 1H nmr (DMSO) delta: 1.18 (d, 6H, J=6.9 Hz), 3.19 (septet, 1H, J=6.9 Hz), 3.81 (s, 3H), 5.16 (s 2H), 6.88 (s, 1H), 7.50 (s, 1H).

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