Potassium Carbonate → HCID 57804187, compound

HRID 2102890Notes

Reaction equation

HRID 2102890 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[OH:13].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CN(C=O)C>[O:27]1[CH2:28][CH2:29][N:24]([CH2:23][CH2:22][O:13][C:3]2[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=2[Br:1])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:25][CH2:26]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 12134897Ethyl 4-bromo-3-hydroxybenzoate

Product 1

HCID 57804187HCID 57804187, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 4-bromo-3-hydroxybenzoate (1.5 g, 6.12 mmol), potassium carbonate (2.5 g, 18.37 mmol) and 4-(2-chloroethyl)morpholine hydrochloride (1.4 g, 7.35 mmol) were placed in 50 mL DMF and the reaction was heated at 80° C. for 18 h. The mixture was cooled and partitioned between EtOAc and water. The organic layer was separated, washed with water, brine, dried (Na2SO4), filtered, and the filtrate was concentrated to an oil. Purification by column chromatography on silica gel using 0-50% EtOAc/hexane as eluent gave the product (1.0 g, 47%) as a colorless oil.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between EtOAc and water
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated to an oil
  8. customPurification by column chromatography on silica gel using 0-50% EtOAc/hexane as eluent

Sources & evidence

ORD record
ord-df6fa7db68c64e0b9221bdfd093889d7
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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