Sodium Carbonate → 4-(2-Bromoethyl)-1,2-dimethylbenzene

HRID 1742711Notes

Reaction equation

HRID 1742711 reaction equation
P(Br)(Br)[Br:2].[CH3:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[CH2:9][CH2:10]O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl.O>[CH3:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[CH2:9][CH2:10][Br:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 339432-(3,4-Dimethylphenyl)ethanol

Product 1

HCID 225073204-(2-Bromoethyl)-1,2-dimethylbenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

Phosphorus tribromide (0.82 g) was added dropwise to a solution of 3,4-dimethylphenethyl alcohol (1.27 g--see Preparation 17) in carbon tetrachloride (10 ml). The mixture was heated under reflux for 2.5 hours then cooled to room temperature and basified (pit 8) by the dropwise addition of 10% aqueous sodium carbonate (5 ml). The mixture was then diluted with water (20 ml) and extracted with dichloromethane (3×50 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as a colourless oil, yield, 0.5g.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. extractionextracted with dichloromethane (3×50 ml)
  4. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-908ce39a84834261a6c3f1b81c199a4a
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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