Carbon tetrabromide → HCID 10858994, compound

HRID 260827Notes

Reaction equation

HRID 260827 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11](O)[CH2:12][CH2:13][CH2:14][CH3:15])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:18][CH:11]([C:8]1[CH:9]=[CH:10][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=1)[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11790735HCID 11790735, compound

Product 1

HCID 10858994HCID 10858994, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-(4-isobutylphenyl)pentanol and carbon tetrabromide in tetrahydrofuran was added triphenylphosphine, and the mixture was stirred at room temperature for 30 minutes. Insoluble materials were removed by filtration and the filtrate was concentrated. Hexane was added to the residue and the mixture was filtered again. Concentration of the filtrate gave crude 1-bromo-1-(4-isobutylphenyl)pentane. Sodium was added portionwise to ethylene glycol at 80° C. while stirring. To the resultant solution was added the obtained crude 1-bromo-1-(4-isobutylphenyl)pentane, and the mixture was stirred at 120° C. for 1 hour. After the mixture was cooled, diluted hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated. Silica gel column chromatography of the concentrate afforded the object compound.

Workup

  1. customInsoluble materials were removed by filtration
  2. concentrationthe filtrate was concentrated
  3. additionHexane was added to the residue
  4. filtrationthe mixture was filtered again

Sources & evidence

ORD record
ord-e21f960b87d14c75bd8f1ed4ce6c0830
Source dataset
uspto-grants-1996_06
Patent number
US05530019

Reaction notes

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