تفاعل #448653

معادلة التفاعل

4-Bromophenyl cyclopropyl ketone

hydrazine monohydrate

potassium hydroxide

→

1-bromo-4-(cyclopropylmethyl)benzene

المردود 49.2%

المذيبات

ethylene glycol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture heated
2. 2
   درجة الحرارةto reflux for 1 hour
3. 3
   درجة الحرارةThe reaction mixture was cooled
4. 4
   أخرىpartitioned between water (20 ml) and ethyl acetate (30 ml)
5. 5
   أخرىthe organic layer was separated
6. 6
   استخلاصThe aqueous layer was extracted with ethyl acetate (30 ml)
7. 7
   غسيلthe combined organic phases were washed with 2M hydrochloric acid (15 ml) and water (15 ml)
8. 8
   تجفيفthen dried (MgSO4)
9. 9
   أخرىevaporated
10. 10
    أخرىThe residue was purified by chromatography on a Mega Bond Elut column
11. 11
    غسيلeluting with hexane

الإجراء التجريبي

4-Bromophenyl cyclopropyl ketone (5.63 g), hydrazine monohydrate (2.5 ml) and potassium hydroxide (3.33 g) were added to ethylene glycol (25 ml) and the mixture heated to reflux for 1 hour. The reaction mixture was cooled and partitioned between water (20 ml) and ethyl acetate (30 ml) and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (30 ml) and the combined organic phases were washed with 2M hydrochloric acid (15 ml) and water (15 ml) then dried (MgSO4) and evaporated. The residue was purified by chromatography on a Mega Bond Elut column, eluting with hexane to give 1-bromo-4-(cyclopropylmethyl)benzene (2.6 g); 1H NMR (CDCl3): 0.2 (m, 2 H), 0.55 (m, 2 H), 2.50 (d, 2 H), 7.14 (d, 2 H), 7.41 (d, 2 H); mass spectrum (EI+) 210 (M.)+.

المصدر