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1-(4-Bromophenyl)propan-2-one → 1-(4-Bromophenyl)-2-methylpropan-2-ol

HRID 2223054
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2223054
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[CH3:12][Mg]Br>C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([CH3:12])([OH:11])[CH3:10])=[CH:6][CH:7]=1
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Komponenten

4

Edukt 2

HCID 7363321-(4-Bromophenyl)propan-2-oneHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 3167851-(4-Bromophenyl)-2-methylpropan-2-olAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 4-bromophenylacteone (6.85 g, 32 mmol) in diethyl-ether (100 ml) was cooled to 0° C. and treated with methylmagnesium bromide (23.5 ml of a 3M solution in diethyl-ether, 70 mmol). The reaction mixture was allowed to warm gradually to room temperature. After 2 hours the reaction was quenched by addition of saturated aqueous ammonium chloride (200 ml). The organic phase was separated and washed with saturated sodium chloride (100 ml), dried (sodium sulfate) and reduced in vacuo. Purification by flash column chromatography on silica gel eluting with pentane:dichloromethane (60:40 changing to 0:100, by volume) gave the title compound as a colourless oil (6.23 g, 84%).

Aufarbeitung

  1. customAfter 2 hours the reaction was quenched by addition of saturated aqueous ammonium chloride (200 ml)
  2. customThe organic phase was separated
  3. washwashed with saturated sodium chloride (100 ml)
  4. dry with materialdried (sodium sulfate)
  5. customPurification by flash column chromatography on silica gel eluting with pentane:dichloromethane (60:40 changing to 0:100, by volume)

Quellen und Nachweise

ORD-Eintrag
ord-041b0b648ccd4818976879baba8772b3
Quelldatensatz
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07375100B2

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