Reaktion #624621

Reaktionsgleichung

4-bromo-iodobenzene

isopropylmagnesium chloride lithium chloride

3-methylbutanal

→

(+/−)-1-(4-bromophenyl)-3-methylbutan-1-ol

Ausbeute 79.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   workup.STIRRINGstir for 1 hour
3. 3
   SonstigeThe reaction was then quenched by addition of saturated ammonium chloride (10 mL) and water (40 mL)
4. 4
   workup.ADDITIONThe mixture was diluted with ethyl acetate (50 mL)
5. 5
   Sonstigethe layers were separated
6. 6
   WaschenThe organics were washed with water (50 mL) and brine (25 mL)
7. 7
   Trocknendried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    SonstigePurification by column chromatography (0-50% ethyl acetate in heptane)

Vorschrift

4-bromo-iodobenzene (1.42 g, 5.00 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled to −40° C. A solution of isopropylmagnesium chloride lithium chloride (5 mL, 1.3 M in THF) was added dropwise over 5 minutes. The mixture was stirred at −40° C. for 30 minutes, then 3-methylbutanal (0.81 mL, 7.5 mmol) was added. The reaction was allowed to warm to room temperature and stir for 1 hour. The reaction was then quenched by addition of saturated ammonium chloride (10 mL) and water (40 mL). The mixture was diluted with ethyl acetate (50 mL), and the layers were separated. The organics were washed with water (50 mL) and brine (25 mL), dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-50% ethyl acetate in heptane) gave (+/−)-1-(4-bromophenyl)-3-methylbutan-1-ol (958 mg, 79%) as a clear oil. 1H NMR (400 MHz, CDCl3, δ): 7.47-7.41 (m, 2H), 7.22-7.17 (m, 2H), 4.68 (dd, J=8.1, 5.4 Hz, 1H), 1.97 (br.s, 1H), 1.71-1.61 (m, 2H), 1.49-1.39 (m, 1H), 0.94-0.90 (m, 6H).

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