Carbon tetrabromide → 1-(3-Bromopropyl)-4-chlorobenzene

HRID 1616146Notes

Reaction equation

HRID 1616146 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10]O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>ClCCl>[Br:32][CH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 2219714-Chlorobenzenepropanol

Product 1

HCID 98811361-(3-Bromopropyl)-4-chlorobenzeneYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-chlorophenyl)propan-1-ol (0.25 g, 1.46 mmol) in dichloromethane (5.5 mL) cooled at 0° C. was added triphenylphosphine (0.42 g, 1.6 mmol) and carbon tetrabromide (0.51 g, 1.5 mmol) and the reaction was stirred at rt overnight. The reaction was quenched with water and extracted with DCM (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 70% EtOAc/hexanes) to afford 1-(3-bromopropyl)-4-chlorobenzene (0.34 g, quant.). LC-MS: (FA) ES+ 234.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with DCM (2×)
  3. washThe combined organic phases were then washed with water, and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash silica gel chromatography (0% to 70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-48cffd67ccfa4719af8c487912137ae9
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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