4-Bromobenzaldehyde → 1-(4-Bromophenyl)-2-methylpropan-1-ol
Reaktionsgleichung
[CH:1]([Mg]Cl)([CH3:3])[CH3:2].[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1>O1CCCC1>[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]([OH:12])[CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 25 °C
Versuchsvorschrift
A solution of isopropylmagnesium chloride (17.0 L, 1M in tetrahydrofuran) was added dropwise to the solution of 4-bromobenzaldehyde (2.1 g, 11.4 mol) in tetrahydrofuran (30 mL) at −10° C. Then the mixture was stirred at 25° C. for 4 hours. The resultant reaction was quenched with saturated ammonium chloride aqueous (20 mL). The organic phase was separated, dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1) to give 1-(4-bromophenyl)-2-methylpropan-1-ol (620 mg, 24%). 1H NMR (300 MHz, CDCl3): δ 7.98-7.85 (m, 2H), 7.48-7.35 (m, 2H), 5.17 (s, 1H), 4.49 (d, J=6.6 Hz, 1H), 2.35-2.30 (m, 1H), 1.01 (d, J=6.6 Hz, 6H).