Water → p-Bromophenyl propionate

HRID 1489185

Reaction equation

HRID 1489185 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.[C:16](Cl)(=[O:19])[CH2:17][CH3:18].O>CN(C)C1C=CN=CC=1.ClCCl>[C:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([Br:8])=[CH:10][CH:11]=1)(=[O:19])[CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 8471TriethylamineHCID 62324Propionyl chloride

Product 1

HCID 90205p-Bromophenyl propionate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (219 ml) was added to a solution of 4-bromophenol (259 g) and 4-dimethylaminopyridine (1.5 g) in dichloromethane (1000 ml) at 0° C. at such a rate that the temperature did not rise above 20° C. When the addition was complete propionyl chloride (137 ml) was added in portions over 1 hour such that the temperature did not rise above 20° C. Finally, the mixture was stirred at room temperature for 2 hours. Water (700 ml) was added and the layers were separated. The dichloromethane solution was washed with brine (500 ml), dried (MgSO4) and concentrated in vacuo to give the title compound as an oil, 344 g.

Workup

  1. customdid not rise above 20° C
  2. additionWhen the addition
  3. additionwas added in portions over 1 hour such that the temperature
  4. customdid not rise above 20° C
  5. customthe layers were separated
  6. washThe dichloromethane solution was washed with brine (500 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18e97558a3014f24875cdb5f4e4d3b20
Source dataset
uspto-grants-1997_10
Patent number
US05677324

Linked notes

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