Potassium Carbonate → HCID 17352815, compound

HRID 1987905Notes

Reaction equation

HRID 1987905 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].Br[C:8]([Br:11])([CH3:10])C.[K].[CH3:13][O:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[OH:24]>CN(C=O)C>[Br:11][CH2:8][CH2:10][CH2:1][O:24][C:16]1[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=1[O:14][CH3:13]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 116582,2-DibromopropaneHCID 767382-Methoxy-4-nitrophenolHCID 5462222Potassium

Product 1

HCID 17352815HCID 17352815, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of K2CO3 (2.0 g, 14.5 mmol), dibromopropane (8.8 g, 43.4 mmol) and the potassium salt of 2-methoxy-4-nitrophenol (3.0 g, 14.5 mmol) in DMF (50 mL) was heated at 80° C. for 24 hr. After removal of any precipitate by filtration, the filtrate was partitioned between EtOAc/H2O (100/20 mL). The organic layer was washed with brine and dried over MgSO4. After removal of the solvent under vacuum, the residue was chromatographed on silica gel using 5%-20% gradient EtOAc/hexanes to elute the title compound as a yellow brownish solid (1.5 g, 36%) MS (ESI) 292 (M+H)+.

Workup

  1. customAfter removal of any precipitate
  2. filtrationby filtration
  3. customthe filtrate was partitioned between EtOAc/H2O (100/20 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customAfter removal of the solvent under vacuum
  7. customthe residue was chromatographed on silica gel using 5%-20% gradient EtOAc/hexanes
  8. washto elute the title compound as a yellow brownish solid (1.5 g, 36%)

Sources & evidence

ORD record
ord-abac6d19909e4b478ee192a6451c0983
Source dataset
uspto-grants-2009_06
Patent number
US07553836B2

Reaction notes

Loading…