Methyl 2-bromo-4-methylbenzoate → 1-(2-Bromo-4-methylphenyl)cyclopentanol

HRID 1037112Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037112
[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[Mg]([CH2:15][CH2:16][CH2:17][CH2:18][Mg]Br)Br>C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]1([OH:6])[CH2:18][CH2:17][CH2:16][CH2:15]1

Komponenten

4

Edukt 2

HCID 21779704Methyl 2-bromo-4-methylbenzoateHCID 178419681HCID 178419681, Verbindung

Produkt 1

HCID 726983321-(2-Bromo-4-methylphenyl)cyclopentanolAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-bromo-4-methylbenzoate (5.0 g, 21.3 mmol) in THF (20 mL) was added dropwise BrMg(CH2)4MgBr (50 mL, 25.5 mmol) at 0° C. under nitrogen and then stirred at rt overnight. The reaction mixture was quenched with aqueous NH4Cl and extracted with EA. The combined organic layer was washed with aqueous NaHCO3 solution and brine, dried over Na2SO4. The solution was concentrated and the residue was purified by column chromatography over silica gel eluted with PE-EA (20:110:1) to provide 1-(2-bromo-4-methylphenyl)-cyclopentanol (4.2 g; yield 78%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.65 (d, 1 H), 7.39 (s, 1 H), 7.10 (d, 1 H), 4.84 (s, 1 H), 2.33 (s, 3 H), 1.89-1.74 (m, 8 H) ppm.

Aufarbeitung

  1. customThe reaction mixture was quenched with aqueous NH4Cl
  2. extractionextracted with EA
  3. washThe combined organic layer was washed with aqueous NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe solution was concentrated
  6. customthe residue was purified by column chromatography over silica gel
  7. washeluted with PE-EA (20:110:1)

Quellen und Nachweise

ORD-Eintrag
ord-8b7fb9976eee497d965eb493f22d77a9
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546357B2

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