Sodium Carbonate → 4-Fluorophenethyl bromide

HRID 1489190Notes

Reaction equation

HRID 1489190 reaction equation
P(Br)(Br)[Br:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13]O)=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl>[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][Br:2])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24614Phosphorus tribromideHCID 820684-Fluorophenethyl Alcohol

Product 1

HCID 5731534-Fluorophenethyl bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Phosphorus tribromide (14 g) was added, over 2 minutes, to a solution of 2-(4-fluorophenyl)ethanol (14 g) in carbon tetrachloride (80 ml). The mixture was heated under reflux for 2 hours then cooled in an ice bath. 10% Aqueous sodium carbonate solution was added until all of the solid has dissolved. The mixture was transferred to a separating funnel and the layers were separated. The aqueous layer was extracted with dichloromethane (50 ml) and the organic solutions were combined, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica eluting with 1:1 hexane/dichloromethane. The product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless oil, 10 g.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethen cooled in an ice bath
  4. dissolutionhas dissolved
  5. customThe mixture was transferred to a separating funnel
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted with dichloromethane (50 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by chromatography on silica eluting with 1:1 hexane/dichloromethane
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f058031209540d4a66df550e364819c
Source dataset
uspto-grants-1997_10
Patent number
US05677324

Reaction notes

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