تفاعل #1857588

ord-acfc42632cdb4413a41b3db25de31c4f

معادلة التفاعل

O
water
C=Cc1c(F)cccc1Br
1-bromo-3-fluoro-2-vinylbenzene
[Li][CH2]CCC
n-butyllithium
O
water
CN(C)C=O
N,N-dimethylformamide
C=Cc1c(F)cccc1C=O
3-fluoro-2-vinylbenzaldehyde

المذيبات

ظروف التفاعل

درجة الحرارة
-78°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةwarmed to room temperature
  2. 2
    استخلاصextracted with ethyl acetate
  3. 3
    تجفيفThe combined organic phases were dried over sodium sulphate
  4. 4
    تركيزconcentrated
  5. 5
    أخرىPurification by column chromatography

الإجراء التجريبي

To a solution of 1-bromo-3-fluoro-2-vinylbenzene (900 mg) in THF (40 ml) was added dropwise, at −78° C., n-butyllithium (3.4 ml 1.6 M/hexane). After 60 minutes, N,N-dimethylformamide (0.69 ml) was added dropwise at −78° C. After stirring at −78° C. for 60 minutes, the reaction mixture was admixed with water and then warmed to room temperature. Then the mixture was admixed with water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated. Purification by column chromatography gives 3-fluoro-2-vinylbenzaldehyde (160 mg).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09247748B2uspto-grants-2016_02