Hydrogen Peroxide → 3-(4-Bromo-3,5-dimethylphenyl)propan-1-ol

HRID 237533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237533
[CH2:1]([C:4]1[CH:5]=[C:6]([CH3:12])[C:7]([Br:11])=[C:8]([CH3:10])[CH:9]=1)[CH:2]=[CH2:3].C12BC(CCC1)CCC2.[OH-:22].[Na+].OO>O1CCCC1>[Br:11][C:7]1[C:6]([CH3:12])=[CH:5][C:4]([CH2:1][CH2:2][CH2:3][OH:22])=[CH:9][C:8]=1[CH3:10]

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonane2×HCID 866971955-Allyl-2-bromo-1,3-dimethylbenzene

Produkt 1

HCID 866971963-(4-Bromo-3,5-dimethylphenyl)propan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 5-allyl-2-bromo-1,3-dimethylbenzene (1.0 g) is cooled to 0° C., 9-borabicyclo[3.3.1]nonane (9-BBN, 26 mL of a 0.5 M solution in tetrahydrofurane) is added dropwise and the mixture is stirred for 2 hours at room temperature. After cooling to 0° C. NaOH (6.7 mL, 4 M) and H2O2 (6.7 mL, 35%) are added dropwise. The mixture is stirred for 12 hours while warming to room temperature. Then the mixture is partitioned between brine and diethylether. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→70:30) to give the title compound. Yield: 750 mg; LC (method 8): tR=0.28 min; Mass spectrum (ESI+): m/z=260 [M+NH4]+.

Aufarbeitung

  1. temperatureAfter cooling to 0° C
  2. stirringThe mixture is stirred for 12 hours
  3. temperaturewhile warming to room temperature
  4. customThen the mixture is partitioned between brine and diethylether
  5. dry with materialThe organic phase is dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→70:30)

Quellen und Nachweise

ORD-Eintrag
ord-78779cab0b114c9985316c41dfa1d816
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642585B2

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