Potassium Iodide → HCID 68087731, compound

HRID 2403599Notes

Reaction equation

HRID 2403599 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:9].Br[CH2:11][CH2:12][O:13][CH2:14][CH2:15]Br.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:4][C:3]=1[Cl:9]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 888884-Bromo-3-chloroaniline

Product 1

HCID 68087731HCID 68087731, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Bromo-3-chloroaniline (500 mg) was dissolved in DMF (10 ml), and bis(2-bromoethyl)ether (1.12 g), K2CO3 (1.34 g), and potassium iodide (80 mg) were added thereto, followed by stirring at 80° C. for 2 days. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was dried over MgSO4 and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (0% to 20% EtOAc/hexane) to obtain 4-(4-bromo-3-chlorophenyl)morpholine (263 mg).

Workup

  1. extractionfollowed by extraction with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (0% to 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-90e436a959164d40ab8c094946564425
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

Loading…