Water → ethyl [2-(3-Bromopropyl)phenyl]acetate

HRID 46993Notes

Reaction equation

HRID 46993 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].P(Br)(Br)[Br:18].O>CCOCC>[Br:18][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 53980166Ethyl [2-(3-Hydroxypropyl)phenyl]acetate

Product 1

HCID 53808728ethyl [2-(3-Bromopropyl)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of ethyl [2-(3-hydroxypropyl)phenyl]acetate (44.4 g., 0.20 mole) in ether (300 ml.) is added dropwise during 40 minutes a solution of phosphorus tribromide (20.7 g., 0.075 mole) in ether (100 ml.). The temperature is maintained at 25°-28° C. during this time by means of a cold water bath. The reaction solution is then heated at reflux for 4 hours. It is cooled and poured into iced-water. The ether layer is separated, washed with water, dried over magnesium sulfate, and evaporated in vacuo to yield ethyl [2-(3-Bromopropyl)phenyl]acetate.

Workup

  1. temperatureThe temperature is maintained at 25°-28° C. during this time by means of a cold water bath
  2. temperatureThe reaction solution is then heated
  3. temperatureat reflux for 4 hours
  4. temperatureIt is cooled
  5. customThe ether layer is separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-9c9d4a2e363044a28f103ba26ba17550
Source dataset
uspto-grants-1979_11
Patent number
US04175203

Reaction notes

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