تفاعل #48042

معادلة التفاعل

NH4Cl

Cyclobutanone

1,4-dibromobenzene

n-BuLi

→

1-(4-bromophenyl)-cyclobutanol

المردود 34.3%

المذيبات

Water

ether

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction mixture was stirred at −78° C. for 15 min
2. 2
   درجة الحرارةslowly (over 2 h) warmed to 0° C.
3. 3
   workup.STIRRINGstirred for a further 1 h
4. 4
   استخلاصthe reaction mixture was extracted with ether
5. 5
   غسيلThe organic layer was washed with brine
6. 6
   تجفيفdried (MgSO4)
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىto give a residue which
10. 10
    أخرىwas purified by flash column chromatography (1:4 ether/pentane)

الإجراء التجريبي

To a solution of 1,4-dibromobenzene (1.00 g, 4.24 mmol) at −78° C. in ether (20 ml) was added n-BuLi (2.65 ml, 1.6 M solution in hexane, 4.24 mmol) and the reaction mixture was stirred at −78° C. for 30 min. Cyclobutanone (348 μl, 4.66 mmol) was then added and the reaction mixture was stirred at −78° C. for 15 min. The reaction mixture was then slowly (over 2 h) warmed to 0° C. and stirred for a further 1 h. Water was added followed by sat. NH4Cl and the reaction mixture was extracted with ether. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography (1:4 ether/pentane) to give 1-(4-bromophenyl)-cyclobutanol (330 mg, 34%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.50 (d, J=8.5 Hz, 2H), 7.38 (d, J=8.5 Hz, 2H), 2.57-2.48 (m, 2H), 2.41-2.31 (m, 2H), 2.02 (m, 1H), 1.69 (m, 1H).

المصدر