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

HRID 1742708Notes

Reaction equation

HRID 1742708 reaction equation
P(Br)(Br)[Br:2].[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[Cl:15])[CH2:9][CH2:10]O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[Cl:15])[CH2:9][CH2:10][Br:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 2445582-(3,4-Dichlorophenyl)ethanol

Product 1

HCID 151493894-(2-Bromoethyl)-1,2-dichlorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Phosphorus tribromide (2.17 g) was added, dropwise, to a solution of 3,4-dichlorophenethyl alcohol (4.26 g) in carbon tetrachloride (30 ml). The mixture was stirred at room temperature for 10 minutes then heated under reflux for 2 hours. 5% Aqueous sodium carbonate (10 ml) was added dropwise and the mixture was extracted with dichloromethane (3×70 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give a yellow oil which was purified by column chromatography on silica eluting with dichloromethane containing hexane (30% down to 0%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless oil, yield, 1.8 g.

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 2 hours
  3. extractionthe mixture was extracted with dichloromethane (3×70 ml)
  4. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a yellow oil which
  7. customwas purified by column chromatography on silica eluting with dichloromethane
  8. additioncontaining hexane (30% down to 0%)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e60d9d88a524108a7bf0e6223731a99
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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