反応 #48042

反応方程式

NH4Cl

Cyclobutanone

1,4-dibromobenzene

n-BuLi

→

1-(4-bromophenyl)-cyclobutanol

収率 34.3%

溶媒

Water

ether

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction mixture was stirred at −78° C. for 15 min
2. 2
   温度slowly (over 2 h) warmed to 0° C.
3. 3
   workup.STIRRINGstirred for a further 1 h
4. 4
   抽出the reaction mixture was extracted with ether
5. 5
   洗浄The organic layer was washed with brine
6. 6
   乾燥dried (MgSO4)
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   その他to give a residue which
10. 10
    その他was purified by flash column chromatography (1:4 ether/pentane)

実験手順

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).

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