반응 #715389

반응 방정식

n-BuLi

1,4-dibromobenzene

2-hexanone

→

6

수율 91.5%

1-Bromo-4-(1-hydroxy-1-methylpentyl)benzene

수율 91.5%

용매

THF

반응 조건

후처리

1. 1
   온도the solution was warmed to room temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   기타The reaction mixture was quenched with water
4. 4
   기타the organic layer was separated
5. 5
   세척Next, the organic phase was washed with water
6. 6
   건조dried over Na2SO4
7. 7
   농축concentrated on a rotary evaporator
8. 8
   기타to give a crude oil
9. 9
   기타The crude was purified by column chromatography (silica gel, chloroform)

실험 절차

n-BuLi (2.5 M in hexanes, 17.0 mL, 42.5 mmol) was added dropwise to a solution of 1,4-dibromobenzene (10.04 g, 42.5 mmol) in THF (100 mL) at −78° C. under nitrogen. After stirring at −78° C. for 1 hour, 2-hexanone (4.5 g, 44.9 mmol) was added dropwise, and the solution was warmed to room temperature and stirred overnight. The reaction mixture was quenched with water and the organic layer was separated. Next, the organic phase was washed with water, dried over Na2SO4, and concentrated on a rotary evaporator to give a crude oil. The crude was purified by column chromatography (silica gel, chloroform) to give 6 as a colorless oil (10.0 g, 91% yield). 1H NMR (500 MHz, CDCl3) δ 7.45 (d, J=8.8 Hz, 2H), 7.30 (d, J=8.8 Hz, 2H), 1.79-1.75 (m, 2H), 1.68 (s, 1H), 1.54 (s, 3H), 1.24-1.28 (m, 4H), 0.85 (t, 3H).

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