Carbon tetrabromide → 1-Bromo-4-(3-bromopropyl)benzene

HRID 1662846Notes

Reaction equation

HRID 1662846 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10]O)=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:32]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][Br:32])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 105606143-(4-Bromophenyl)propan-1-ol

Product 1

HCID 151535781-Bromo-4-(3-bromopropyl)benzeneYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of intermediate 49 (Example 99) (4.0 g, 19 mmol) in THF (30 mL) at 0° C. under the argon atmosphere was added PPh3 (6.3 g, 24 mmol) followed by CBr4 (8.0 g, 24 mmol). The mixture was stirred at the same temperature for 15 min and then stirred at room temperature for additional 15 h. Most of the solvent was removed and the residue purified by flash chromatography on silica gel (hexane) to afford the title compound (3.5 g, 66%) as a colorless oil.

Workup

  1. stirringstirred at room temperature for additional 15 h
  2. customMost of the solvent was removed
  3. customthe residue purified by flash chromatography on silica gel (hexane)

Sources & evidence

ORD record
ord-715c30fe887747d9a70bba84d5d325df
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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