تفاعل #54992

ord-242c5be1cd6e4e03bc6ce430f2e03d00

معادلة التفاعل

C#Cc1ccc(-c2ccc(F)cc2)cc1
4-ethynyl-4'-fluorobiphenyl
C[CH2][Mg][Br]
ethyl magnesium bromide
C1CO1
ethylene oxide
Fc1ccc(-c2ccc(C#CCC[O][Mg][Br])cc2)cc1
4-(4'-Fluoro-4-biphenylyl)-3-butyn-1-oxymagnesium bromide

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONto which is added 100 ml
  2. 2
    أخرىAfter subsidance of the exothermic reaction
  3. 3
    درجة الحرارةthe mixture is heated
  4. 4
    درجة الحرارةunder reflux for 1 hour

الإجراء التجريبي

19.6 g. of 4-ethynyl-4'-fluorobiphenyl in 200 ml. THF is converted with an excess of ethyl magnesium bromide to the Grignard compound, to which is added 100 ml. of THF and then a solution of 5 g. of ethylene oxide in 10 ml. of THF. After subsidance of the exothermic reaction, the mixture is heated under reflux for 1 hour. 4-(4'-Fluoro-4-biphenylyl)-3-butyn-1-oxymagnesium bromide is thereby formed in situ. To this is added 150 ml. of 1 N hydrochloric acid. After stirring for 20 minutes at 20° and the usual work up, 4-(4'-fluoro-4-biphenylyl)-3-butyn-1-ol, m.p. 134°, is obtained.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04151294uspto-grants-1979_04