반응 #65700

반응 방정식

Thiophenol

KCN 18-crown-6

potassium carbonate

chloride

1-bromo-3-chloro-2-methylpropane

→

2,3,4,5-tetrahydro-3-methyl-1-benzothiepine

용매

acetone

acetonitrile

반응 조건

실험 절차

Thiophenol was alkylated with 1-bromo-3-chloro-2-methylpropane in the presence of potassium carbonate (K2CO3) in acetone. The resulting primary chloride was lengthened by one carbon atom using KCN/18-crown-6 in acetonitrile. Basic hydrolysis, ring closure with polyphosphoric acid in analogy to Example 17(C) and Wolf-Kishner reduction according to Example 17(D) finally gave the required 2,3,4,5-tetrahydro-3-methyl-1-benzothiepine as a colorless oil.

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