4-Bromophenol → p-Bromophenyl propionate

HRID 1416174Notes

Reaction equation

HRID 1416174 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:19])[CH2:17][CH3:18]>CN(C)C1C=CN=CC=1.ClCCl>[C:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:19])[CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 8471TriethylamineHCID 62324Propionyl chloride

Product 1

HCID 90205p-Bromophenyl propionate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Bromophenol (259 g) and 4-dimethylaminopyridine (1.5 g) were dissolved in dichloromethane (1000 ml), the solution was cooled in an ice bath and triethylamine (219 ml) was added portionwise such that the reaction temperature was kept below 20° C. Propionyl chloride (137 ml) was then added over 1 hour and the resulting mixture was stirred at room temperature for 2 hours. The mixture was washed with water followed by brine, then dried (anhydrous magnesium sulphate) and the solvent removed under reduced pressure to yield 4-bromophenyl propionate (344 g) as a green oil.

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. customwas kept below 20° C
  3. washThe mixture was washed with water
  4. dry with materialdried (anhydrous magnesium sulphate)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e23305ecedd6434f86a9cdf31e6750fb
Source dataset
uspto-grants-1999_06
Patent number
US05912244

Reaction notes

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