Carbon tetrabromide → HCID 22400554, compound

HRID 260821Notes

Reaction equation

HRID 260821 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:19][CH2:20][CH3:21])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]O)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].C(Br)(Br)(Br)[Br:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:23][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:11]([C:8]1[CH:9]=[CH:10][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=1)[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22400477HCID 22400477, compound

Product 1

HCID 22400554HCID 22400554, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 7-(4-isobutylphenyl)-1-decanol and carbon tetrabromide in tetrahydrofuran was added portionwise triphenylphosphine. The mixture was stirred at room temperature for 2 hours and insoluble materials were filtered off. The filtrate was concentrated and n-hexane was added thereto, then the mixture was filtered again and the filtrate was concentrated. The residue was chromatographed on a silica gel column (n-hexane as eluent) to give the object compound as an oil.

Workup

  1. filtrationinsoluble materials were filtered off
  2. concentrationThe filtrate was concentrated
  3. additionn-hexane was added
  4. filtrationthe mixture was filtered again
  5. concentrationthe filtrate was concentrated
  6. customThe residue was chromatographed on a silica gel column (n-hexane as eluent)

Sources & evidence

ORD record
ord-814a26caa6a6424c8c501193aa0e1f5e
Source dataset
uspto-grants-1996_06
Patent number
US05530019

Reaction notes

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