Phenol → 7-Phenoxyheptyl bromide

HRID 2228899Notes

Reaction equation

HRID 2228899 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 783091,7-Dibromoheptane

Product 1

HCID 105162527-Phenoxyheptyl bromide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of phenol (0.58 g) and 1,7-dibromoheptane (4.76 g) in dimethylformamide (5 ml) was added potassium carbonate (4.3 g) and the mixture was heated at 80° C. for 6 h. The mixture was cooled and the solvent was removed under reduced pressure. Toluene (10 ml) was added and removed under reduced pressure. The residue was chromatographed on silica gel using hexane as eluent. This gave 1-bromo-7-phenoxyheptane (1.15 g). 1H-NMR (CDCl3) δ 1.3-1.7 (6H, m), 1.7-2.1 (4H, m), 3.41 (2H, t), 3.95 (2H, t), 6.8-7.0 (3H, m) and 7.2-7.4 (2H, m).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was removed under reduced pressure
  3. additionToluene (10 ml) was added
  4. customremoved under reduced pressure
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-0210eddb004343a7b751a7f6af06d5aa
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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