Hydrochloric Acid → Benzene, (2-bromoethoxy)-

HRID 1244195Notes

Reaction equation

HRID 1244195 reaction equation
[O:1]([CH2:8][CH2:9]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:12].Cl>N1C=CC=CC=1>[Br:12][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Conditions

Temperature
50 °C

Procedure

To 3.25 ml (0.04 mmol) of pyridine were added 13.82 g (0.1 mol) of 2-phenoxy ethanol and 10.83 g (0.04 mol) of phosphorus tribromide, followed by reacting at 0° C. for 1 hour while stirring. The reaction solution was warmed up to 50° C. and then reacted for 1 hour while stirring. After completion of the reaction, excess 1N hydrochloric acid (0° C.) were added to the reaction solution and then subjected to an extraction procedure using chloroform. The resulting organic layer was washed with 1N hydrochloric acid, water and an aqueous solution of sodium hydrogen carbonate, then dried on magnesium sulfate and concentrated under a reduced pressure. An obtained crude product was purified by distillation to obtain 9.5 g of a desired 2-bromoethylphenyl ether (yield 47%).

Workup

  1. customreacted for 1 hour
  2. stirringwhile stirring
  3. additionwere added to the reaction solution
  4. extractionsubjected to an extraction procedure
  5. washThe resulting organic layer was washed with 1N hydrochloric acid, water
  6. dry with materialan aqueous solution of sodium hydrogen carbonate, then dried on magnesium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customAn obtained crude product
  9. distillationwas purified by distillation

Sources & evidence

ORD record
ord-5a59f01e61864fc0920a69bf837a8461
Source dataset
uspto-grants-2006_10
Patent number
US07122499B2

Reaction notes

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