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

HRID 237533Notes

Reaction equation

HRID 237533 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-78779cab0b114c9985316c41dfa1d816
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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